α-phenyl-βketosulfone

ABSTRACT

The present invention relates to novel aryl-substituted S(O) m  cycles of the formula (I)                    
     in which F 1 , F 2 , G, V, W, X, Y, Z and m are each as defined in the description, to processes for their preparation and to their use in agriculture, for example as crop protection agents (fungicides, herbicides and insecticides).

The present invention relates to novel aryl-substituted S(O)_(m) cycles(α-phenyl-β-keto sulphones), to a plurality of processes for theirpreparation and to their use in agriculture, for example as cropprotection agents (for example as fungicides, herbicides andinsecticides).

4-Amino-5-phenyl-3-ethyl-2-methyl-2,3-dihydroisothiazole 1,1-dioxide (J.L. Marco et al., Tetrahedron Letters 39, 4123 (1998)),4-amino-5-phenyl-3,3-dimethyl-2-benzyl-2,3-dihydroisothiazole1,1-dioxide and4-amino-5-phenyl-3,3-dimethyl-2-(3-chloro-benzyl)-2,3-dihydroisothiazole1,1-dioxide (S. T. Ingate, et al., Tetrahedron 53, 17795 (1997)) areknown from the literature. Also known are2-methyl-5-phenyl-isothiazolidin-4-one 1,1-dioxide,2,3-dimethyl-5-phenyl-isothiazolidin-4-one 1,1-dioxide and5-phenyl-2,3,3-trimethyl-isothiazolidin-4-one 1,1-dioxide (H.-D.Stachel, G. Drasch, Archiv Pharm. 318, 304 (1985)). Use of thesecompounds as crop protection agents or pesticides has hitherto not beendisclosed.

Furthermore known are 3-phenyl-1,2-oxathiolan-4-one 2,2-dioxide,5-methyl-3-phenyl-1,2-oxathiolan-4-one 2,2-dioxide,5,5-dimethyl-3-phenyl-1,2-oxathiolan-4-one 2,2-dioxide (H. D. Stachel,G. Drasch, Archiv Pharm. 318, 304 (1985)),5-amino-5,5-dimethyl-3-phenyl-1,2-oxathiolane 2,2-dioxide and4-amino-5-methyl-3-phenyl-5-phenylmethyl-1,2-oxathiolane 2,2-dioxide (S.T. Ingate et al., Tetrahedron 53, 17795 (1997)). Use of these compoundsas crop protection agents or pesticides has hitherto not been disclosed.

2-Arylbenzo[b]thiophen-3(2H)-one 1,1-dioxides have been disclosed foruse as anti-inflammatory agents and anticoagulants (J. G. Lombardino, E.H. Wiseman, J. Med. Chem., 13, 206 (1970)). Also known is2-phenyl-3-keto-tetrahydrothiophene 1,1-dioxide (A. Abdel-Wahab et al.,Phosphorus, Sulfur and Silicon, 59, 149 (1991)). Furthermore known are2-phenylbenzo[b]thiophene-3-amine, 2-phenylbenzo[b]-thiophene-3-amine1-oxide and 2-phenylbenzo[b]thiophene-3-amine 1,1-dioxide (J. R. Beck,J. Heterocyclic Chem. 15, 513 (1978)). Likewise, a use of thesecompounds as crop protection agents or pesticides has hitherto not beendisclosed.

This invention, accordingly, provides aryl-substituted S(O)_(m) cyclesof the general formula (I)

in which

V, W, X, Y and Z independently of one another each represent hydrogen,halogen, nitro, cyano or a radical from the group consisting of alkyl,alkenyl, alkinyl, alkoxy, S(O)_(n)-alkyl, halogenoalkyl, halogenoalkoxy,in each case optionally substituted aryl, phenylalkyl, aryloxy,phenyl-alkyloxy or aryl-S(O)_(n)—, where two adjacent radicals togetherwith the carbon atoms to which they are attached form an optionallysubstituted ring which is optionally interrupted by one or moreheteroatoms;

with the proviso that at least one radical of the substituents V, W, X,Y or Z has to be different from hydrogen,

n represents the numbers 0 to 2,

m represents the numbers 1 and 2,

F¹ and F² represent one of the groups

in which

A represents hydrogen, in each case optionally halogen-substitutedalkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturatedor unsaturated, optionally substituted cycloalkyl in which optionally atleast one ring atom is replaced by a heteroatom, or represents in eachcase optionally halogen-, alkyl-, halogenoalkyl-, alkoxy-,halogenoalkoxy-, cyano- or nitro-substituted aryl, arylalkyl or hetaryl,

B represents hydrogen, alkyl or alkoxyalkyl, or

A and B together with the carbon atom to which they are attachedrepresent a saturated or unsaturated, unsubstituted or substituted cyclewhich optionally contains at least one heteroatom,

D represents hydrogen or an optionally substituted radical from thegroup consisting of alkyl, alkenyl, alkinyl, alkoxyalkyl,polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionallysubstituted cycloalkyl in which optionally one or more ring members arereplaced by heteroatoms, represents optionally substituted arylalkyl,aryl, hetarylalkyl, hetaryl or CO—R¹¹, or

A and D together with the atoms to which they are attached represent asaturated or unsaturated cycle which is unsubstituted or substituted inthe A,D-moiety and optionally contains at least one (in the case of—F¹—F²=(4) further) heteroatom, or

A and Q¹ together represent alkanediyl or alkenediyl, each of which isoptionally substituted by in each case optionally substituted alkyl,hydroxyl, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl, or representan optionally substituted alkanedienediyl, with the proviso that B andQ² together with the carbon atoms to which they are attached represent adouble bond and at least one of the substituents W or X does notrepresent hydrogen,

Q¹ represents hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, saturated orunsaturated, optionally substituted cycloalkyl in which optionally oneor more ring members are replaced by heteroatoms, or representsoptionally substituted phenyl,

Q² represents hydrogen or alkyl,

G represents hydroxyl (a) or represents one of the groups

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur,

M represents oxygen or sulphur,

R¹ represents in each case optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionallyhalogen-, alkyl- or alkoxy-substituted cycloalkyl in which one or moremethylene groups may be replaced by heteroatoms, or represents in eachcase optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkylor hetaryloxyalkyl,

R² represents in each case optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each caseoptionally substituted cycloalkyl, phenyl or benzyl,

R³, R⁴ and R⁵ independently of one another each represent in each caseoptionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino,alkylthio, alkenylthio, cycloalkylthio and represent in each caseoptionally substituted phenyl, benzyl, phenoxy or phenylthio and

R⁶ and R⁷ independently of one another each represent hydrogen, in eachcase optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy,alkoxyalkyl, represent optionally substituted phenyl, representoptionally substituted benzyl, or together with the N atom to which theyare attached represent an optionally substituted ring which isoptionally interrupted by oxygen or sulphur,

R⁸ represents in each case optionally halogen-substituted alkyl,alkoxyalkyl, alkenyl, alkenyloxyalkyl, alkinyl, alkinyloxyalkyl,alkylcarbonylalkyl, alkoxycarbonylalkyl or represent optionallysubstituted cycloalkyl or represent optionally substituted arylalkyl,arylcarbonylalkyl or phenoxyalkyl,

R⁹ and R¹⁰ independently of one another each represent hydrogen, alkyl,alkenyl, alkoxyalkyl, alkylthioalkyl, represent cycloalkyl which isoptionally interrupted by heteroatoms, represent in each case optionallysubstituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl,or

R⁹ and R¹⁰ together with the nitrogen to which they are attached form a3- to 9-membered ring which is optionally substituted and optionallyinterrupted by further heteroatoms, or

R¹⁰ represents the group CO—R¹¹, where

R¹¹ represents hydrogen, optionally halogen-substituted alkyl, alkenyl,alkoxy, optionally substituted cycloalkyl which may optionally beinterrupted by heteroatoms, or represents optionally substituted aryl,arylalkyl, arylalkyloxy or phenoxy, possible substituents being halogen,nitro, cyano, alkyl, alkoxy, halogenoalkyl and halogenoalkoxy.

Depending inter alia on the nature of the substituents, the compounds ofthe formula (I) can be present as geometric and/or optical isomers orisomer mixtures of different composition which, if appropriate, can beseparated in a customary manner. The present invention provides both thepure isomers and the isomer mixtures, their preparation and use and thecompositions comprising them. However, hereinbelow, for the sake ofsimplicity, compounds of the formula (I) are always referred to,although this may mean both the pure compounds and, if appropriate,mixtures having different proportions of isomeric compounds.

Incorporating the meanings (1) to (4) of the group —F¹—F²—, thefollowing main structures (I-1) to (I-4) result:

in which

A, B, D, G, Q¹, Q², V, W, X, Y, Z and m are each as defined above.

Incorporating the different meanings (a), (b), (c), (d), (e), (f), (g),(h) and (i) of the group G, the following main structures (I-1-a) to(I-1-i) result if —F¹—F²— represents the group (1)

in which

A, B, D, E, L, M, V, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰and m are each as defined above.

Incorporating the different meanings (a), (b), (c), (d), (e), (f), (g),(h) and (i) of the group G, the following main structures (I-2-a) to(I-2-i) result if —F¹—F²— represents the group (2)

in which

A, B, E, L, M, V, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰and m are as defined above.

Incorporating the different meanings (a), (b), (c), (d), (e), (f), (g),(h) and (i) of the group G, the following main structures (I-3-a) to(I-3-i) result if —F¹—F²— represents the group (3)

in which

A, B, Q¹, Q², E, L, M, V, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸,R⁹, R¹⁰ and m are as defined above.

Incorporating the different meanings (a), (b), (c), (d), (e), (f), (g)(h) and (i) of the group G, the following main structures (I-4-a) to(I-4-i) result if —F¹—F²— represents the group (4)

in which

A, D, E, L, M, V, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰and m are each as defined above.

Furthermore, it has been found that the novel compounds of the formula(I) are obtained by one of the processes described below:

(A) Substituted compounds of the formula (I-1-a)

in which

A, B, D, V, W, X, Y, Z and m are each as defined above

are obtained when

amino acid esters of the formula (II)

in which

A, B, D, V, W, X, Y, Z and m are each as defined above and

R¹² represents alkyl (preferably C₁-C₆-alkyl)

are condensed intramolecularly in the presence of a diluent and in thepresence of a base.

(B) Moreover, it has been found that substituted compounds of theformula (I-2-a)

in which

A, B, V, W, X, Y, Z and m are each as defined above

are obtained when

carboxylic acid esters of the formula (III)

in which

A, B, V, W, X, Y, Z, R¹² and m are each as defined above

are condensed intramolecularly in the presence of a diluent and in thepresence of a base.

Furthermore, it has been found

(C) that compounds of the formula (I-3-a)

in which

A, B, Q¹, Q², V, W, X, Y, Z and m are each as defined above

are obtained when

carboxylic acid esters of the formula (IV)

in which

A, B, Q¹, Q², V, W, X, Y, Z and m are each as defined above and

R¹² represents alkyl (in particular C₁-C₈-alkyl)

are cyclized intramolecularly, if appropriate in the presence of adiluent and in the presence of a base.

(D) Furthermore, substituted compounds of the formula (I-4-a)

in which

A, D, V, W, X, Y, Z and m are each as defined above

are obtained when

hydrazides of the formula (V)

in which

A, D, V, W, X, Y, Z and m are each as defined above and

R¹² represents alkyl (in particular C₁-C₆-alkyl) or optionallysubstituted phenyl (in particular halogen- or nitro-substituted phenyl)

are cyclized, if appropriate in the presence of a diluent and in thepresence of a base.

Moreover, it has been found

(E) that the compounds of the formulae (I-1-b) to (I-4-b) shown above inwhich A, B, D, Q¹, Q², R¹, V, W, X, Y, Z and m are each as defined aboveare obtained when compounds of the formulae (I-1-a) to (I-4-a) shownabove in which A, B, D, Q¹, Q², V, W, X, Y, Z and m are each as definedabove are in each case

(α) reacted with acid halides of the formula (VI)

in which

R¹ is as defined above and

Hal represents halogen (in particular chlorine or bromine) or

(β) reacted with carboxylic anhydrides of the formula (VII)

R¹—CO—O—CO—R¹  (VII)

in which

R¹ is as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder;

(F) that the compounds of the formulae (I-1-c) to (I-4-c) shown above inwhich A, B, D, Q¹, Q², R², M, V, W, X, Y, Z and m are each as definedabove and L represents oxygen are obtained when compounds of theformulae (I-1-a) to (I-4-a) shown above in which A, B, D, Q¹, Q², V, W,X, Y, Z and m are each as defined above are in each case

reacted with chloroformic esters or chloroformic thioesters of theformula (VIII)

R²—M—CO—Cl  (VIII)

in which

R² and M are each as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder;

(G) that compounds of the formulae (I-1-c) to (I-4-c) shown above inwhich A, B, D, Q¹, Q², R², M, V, W, X, Y, Z and m are each as definedabove and L represents sulphur are obtained when compounds of theformulae (I-1-a) to (I-4-a) shown above in which A, B, D, Q¹, Q², V, W,X, Y, Z and m are each as defined above are in each case

reacted with chloromonothioformic esters or chlorodithiofornic esters ofthe formula (IX)

in which

M and R² are each as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder, and

(H) that compounds of the formulae (I-1-d) to (I-4-d) shown above inwhich A, B, D, Q¹, Q², R³, V, W, X, Y, Z and m are each as defined aboveare obtained when compounds of the formulae (I-1-a) to (I-4-a) shownabove in which A, B, D, Q¹, Q², V, W, X, Y, Z and m are each as definedabove are in each case

reacted with sulphonyl chlorides of the formula (X)

R³—SO₂—Cl  (X)

in which

R³ is as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder,

(I) that compounds of the formulae (I-1-e) to (I-4-e) shown above inwhich A, B, D, L, Q¹, Q², R⁴, R⁵, V, W, X, Y, Z and m are each asdefined above are obtained when compounds of the formulae (I-1-a) to(I-4-a) shown above in which A, B, D, Q¹, Q², V, W, X, Y, Z and m areeach as defined above are in each case

reacted with phosphorus compounds of the formula (XI)

in which

L, R⁴ and R⁵ are each as defined above and

Hal represents halogen (in particular chlorine or bromine),

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder,

(J) that compounds of the formulae (I-1-f) to (I-4-f) shown above inwhich A, B, D, E, Q¹, Q², V, W, X, Y, Z and m are each as defined aboveare obtained when compounds of the formulae (I-1-a) to (I-4-a) in whichA, B, D, Q¹, Q², V, W, X, Y, Z and m are each as defined above are ineach case

reacted with metal compounds or amines of the formula (XII) or (XIII)

Me(OR¹³)_(t)  (XII)

in which

Me represents a mono- or divalent metal (preferably an alkali metal oralkaline earth metal, such as lithium, sodium, potassium, magnesium orcalcium),

t represents the number 1 or 2 and

R¹³, R¹⁴, R¹⁵ independently of one another each represent hydrogen oralkyl (preferably C₁-C₈-alkyl),

if appropriate in the presence of a diluent,

(K) that compounds of the formulae (I-1-g) to (I-4-g) shown above inwhich A, B, D, L, Q¹, Q², R⁶, R⁷, V, W, X, Y, Z and m are each asdefined above are obtained when compounds of the formulae (I-1-a) to(I-4-a) shown above in which A, B, D, Q¹, Q², V, W, X, Y, Z and m areeach as defined above are in each case

(α) reacted with isocyanates or isothiocyanates of the formula (XIV)

R⁶—N═C═L  (XIV)

in which

R⁶ and L are each as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of a catalyst, or

(β) reacted with carbamoyl chlorides or thiocarbamoyl chlorides of theformula (XV)

in which

L, R⁶ and R⁷ are each as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder,

(L) that compounds of the formulae (I-1-h) to (I-4-h) shown above inwhich A, B, D, Q¹, Q², R⁸, V, W, X, Y, Z and m are each as defined aboveare obtained when compounds of the formulae (I-1-a) to (I-4-a) shownabove in which A, B, D, Q¹, Q², V, W, X, Y, Z and m are each as definedabove are reacted with

compounds of the formula (XVI)

R¹⁰—U  (XVI)

in which

R¹⁰ is as defined above,

U represents chlorine, bromine, iodine and O—SO₂—R¹⁶ and

R¹⁶ represents optionally halogen-substituted alkyl (in particulartrifluoromethyl) or optionally substituted phenyl (in particularmethyl-, chlorine-, bromine- or nitro-substituted phenyl),

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder,

(M) that compounds of the formulae (I-1-i) to (I-4-i) shown above inwhich A, B, D, Q¹, Q², R⁹, R¹⁰, V, W, X, Y, Z and m are each as definedabove, where R¹⁰ does not represent the group CO—R¹¹, are obtained

(α) when compounds of the formulae (I-1-a) to (I-4-a) in which A, B, D,Q¹, Q², V, W, X, Y, Z and m are each as defined above are reacted withcompounds of the formula (XVII)

in which

R⁹ and R¹⁰ are each as defined above and R¹⁰ does not represent thegroup CO—R¹¹

in the presence of a solvent, if appropriate in the presence of anacidic catalyst, with distillative removal of an azeotrope or in thepresence of a dehydrating agent (for example molecular sieve), or

β) when, in the case that R⁹ and R¹⁰ each represent hydrogen, nitrilesof the formula (XVIII)

in which

V, W, X, Y, Z and m are each as defined above and

F¹ and F² represent the groups

in which the radicals A, B, D, Q¹ and Q² are each as defined above arecyclized intramolecularly in the presence of a solvent and in thepresence of a base,

(N) that compounds of the formulae (I-1-i) to (I-4-i) shown above inwhich A, B, D, Q¹, Q², R⁹, V, W, X, Y, Z and m are each as defined aboveand R¹⁰ represents the group CO—R¹¹ are obtained when compounds of theformulae (I-1-i¹) to (I-4-i¹)

in which

F¹, F², R⁹, V, W, X, Y, Z and m are each as defined above

α) are reacted with acid halides of the general formula (XIX)

in which

R¹¹ is as defined above, but does not represent hydrogen,

Hal represents halogen, in particular chlorine or bromine,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder, or

β) are reacted with carboxylic anhydrides of the general formula (XX)

R¹¹—CO—O—CO—R¹¹  (XX)

in which

R¹¹ are as defined above and, independently of one another, areidentical or different, but do not represent hydrogen,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder,

it also being possible to use mixtures of the reagents of the formulae(XVIII) and (XIX), or

γ) are reacted with orthoformic esters of the formula (XXI)

in which

R¹¹ represents hydrogen and

Alk represents C₁-C₄-alkyl (in particular methyl or ethyl),

if appropriate in the presence of a diluent and if appropriate in thepresence of a base.

(O) Moreover, it has been found that compounds of the formula (I-1-i)

shown above in which

A, B, R⁹, R¹⁰, R¹¹, V, W, X, Y, Z and m are each as defined above

are obtained

when compounds of the formula (I- I-i²)

in which

A, B, R⁹, R¹⁰, V, W, X, Y, Z and m are each as defined above

are reacted with acid chlorides of the general formula (XIX)

in which

R¹¹ is as defined above, but does not represent hydrogen,

Hal represents halogen, in particular chlorine and bromine,

if appropriate in the presence of a diluent and preferably in thepresence of a base.

Furthermore, it has been found that the novel compounds of the formula(I) have very good pesticidal activity, preferably as insecticides andacaricides, and also as herbicides.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicalslisted in the formulae mentioned above and below are illustrated below:

V preferably represents hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy, phenyl, nitroor cyano,

W preferably represents hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy, nitro or cyano,

X preferably represents hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkinyl,C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,C₁-C₆-halogenoalkoxy, nitro, cyano or in each case optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl,phenyl-C₁-C₄-alkyl, phenoxy, phenylthio, benzyloxy or benzylthio,

Y and Z independently of one another each preferably represent hydrogen,halogen, C_(1-C) ₆-alkyl, C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy,C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl,C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkoxy, nitro, cyano or in each caseoptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₆-halogenoalkoxy-, nitro- or cyano-substituted phenyl,phenyl-C₁-C₄-alkyl, phenoxy, phenylthio, benzyloxy or benzylthio,

X and V together with the carbon atoms to which they are attachedpreferably represent an optionally halogen- or alkyl-substituted 5- or6-membered ring which may optionally be interrupted by one or twoheteroatoms, with the proviso that Y and Z do not form a ring,

Y and Z together with the carbon atoms to which they are attachedpreferably represent an optionally halogen- or alkyl-substituted 5- or6-membered ring which may optionally be interrupted by one or twoheteroatoms, with the proviso that X and V do not form a ring,

m preferably represents the numbers 1 and 2,

with the proviso that at least one radical of the substituents V, W, X,Y or Z has to be different from hydrogen,

F¹ and F² each preferably represent one of the groups

A preferably represents hydrogen or in each case optionallyhalogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₁-C₁₀-alkoxy-C₁-C₈-alkyl, di-, tri- or tetra-C₁-C₈-alkoxy-C₁-C₈-alkyl,C₁-C₁₀-alkylthio-C₁-C₆-alkyl, optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one or twonot directly adjacent ring members are replaced by oxygen and/orsulphur, or represents in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano- ornitro-substituted C₆- or C₁₀ -aryl (phenyl or naphthyl), hetaryl having5 to 6 ring atoms (for example furanyl, pyridyl, imidazolyl, triazolyl,pyrazolyl, pyrimidyl, thiazolyl or thienyl) or C₆- orC₁₀-aryl-C₁-C₆-alkyl (phenyl-C₁-C₆-alkyl or naphthyl-C₁-C₆-alkyl),

B preferably represents hydrogen, C₁-C₁₂-alkyl orC₁-C₈-alkoxy-C₁-C₆-alkyl, or

A, B and the carbon atom to which they are attached preferably representsaturated C₃-C₁₀-cycloalkyl or unsaturated C₅-C₁₀-cycloalkyl in whichoptionally one ring member is replaced by oxygen or sulphur and whichare optionally mono- or disubstituted by C₁-C₈-alkyl, C₃-C₁₀-cycloalkyl,C₁-C₈-halogenoalkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, halogen or phenyl,or

A, B and the carbon atom to which they are attached preferably representC₃-C₆-cycloalkyl which is substituted by an alkylenediyl group whichoptionally contains one or two not directly adjacent oxygen and/orsulphur atoms, or by an alkylenedioxyl or by an alkylenedithioyl groupwhich, together with the carbon atom to which it is attached, forms afurther five- to eight-membered ring, or

A, B and the carbon atom to which they are attached preferably representC₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl in which two substituentstogether with the carbon atoms to which they are attached represent ineach case optionally C₁-C₆-alkyl-, C₁-C₆-alkoxy- or halogen-substitutedC₂-C₆-alkanediyl, C₂-C₆-alkenediyl or C₄-C₆-alkanedienediyl in whichoptionally one methylene group is replaced by oxygen or sulphur,

D preferably represents hydrogen, in each case optionallyhalogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkinyl,C₁-C₁₀-alkoxy-C₂-C₈-alkyl, di-, tri- or tetra-C₁-C₁₈-alkoxy-C₂-C₈-alkyl,C₁-C₁₀-alkylthio-C₂-C₈-alkyl, optionally halogen-, C₁-C₄-alkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkyl-substituted C₃-C₈-cycloalkyl inwhich optionally one ring member is replaced by oxygen or sulphur, orrepresents in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano- ornitro-substituted phenyl, hetaryl having 5 or 6 ring atoms (for examplefuranyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl,thienyl or triazolyl), phenyl-C₁-C₆-alkyl or hetaryl-C₁-C₆-alkyl having5 or 6 ring atoms (for example furanyl-, imidazolyl-, pyridyl-,thiazolyl-, pyrazolyl-, pyrimidyl-, pyrrolyl-, thienyl- ortriazolyl-C₁-C₆-alkyl) or represents the group CO—R¹¹, or A and Dtogether preferably represent in each optionally substitutedC₃-C₆-alkanediyl or C₃-C₆-alkenediyl in which optionally one methylenegroup is replaced by a carbonyl group, oxygen or sulphur, possiblesubstituents being in each case:

halogen, hydroxyl, mercapto or in each case optionallyhalogen-substituted C₁-C₁₀-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₃-C₇-cycloalkyl, phenyl or benzyloxy, where optionally two adjacentsubstituents together with the carbon atoms to which they are attachedform a further saturated or unsaturated cycle having 5 or 6 ring atoms(in the case of the compound of the formula (I-1), A and D thenrepresent together with the atoms to which they are attached, forexample for the groups AD-1 to AD-10 mentioned further below) which maycontain oxygen or sulphur, or which may optionally contain one of thefollowing groups

or

A and Q¹ together preferably represent C₃-C₆-alkanediyl orC₄-C₆-alkenediyl, each of which is optionally mono- or disubstituted byidentical or different substituents from the group consisting of halogenand hydroxyl, by C₁-C₁₀-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₃-C₇-cycloalkyl, each of which is optionally mono- to trisubstituted byidentical or different substituents from the group consisting ofhalogen, or by benzyloxy or phenyl, each of which is optionally mono- totrisubstituted by identical or different substituents from the groupconsisting of halogen, C₁-C₆-alkyl and C₁-C₆-alkoxy, or representoptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted alkanedienediyl, withthe proviso that B and Q² together with the carbon atoms to which theyare attached represent a double bond and at least one of thesubstituents W or X does not represent hydrogen,

Q¹ preferably represents hydrogen, C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₂-alkyl, C_(1-C) ₆-alkylthio-C₁-C₂-alkyl, optionallyC₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in whichoptionally one methylene group is replaced by oxygen or sulphur, orrepresents optionally halogen-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₂-halogenoalkyl-, C₁-C₂-halogenoalkoxy-, cyano- or nitro-substitutedphenyl, or

Q² preferably represents hydrogen or C₁-C₄-alkyl,

G preferably represents hydroxyl (a) or represents one of the groups

 in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur,

R¹ preferably represents in each case optionally halogen-substitutedC₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl,C₁-C₈-alkylthio-C₁-C₈-alkyl, poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or optionallyhalogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl inwhich optionally one or more (preferably one or two) not directlyadjacent ring members are replaced by oxygen and/or sulphur,

represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-, C₁-C₆-halogenoalkoxy-,C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl,

represents optionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl,

represents optionally halogen- or C₁-C₆-alkyl-substituted 5- or6-membered hetaryl (for example pyrazolyl, thiazolyl, pyridyl,pyrimidyl, furanyl or thienyl),

represents optionally halogen- or C₁-C₆-alkyl-substitutedphenoxy-C₁-C₆-alkyl, or

represents optionally halogen-, amino- or C₁-C₆-alkyl-substituted 5- or6-membered hetaryloxy-C₁-C₆-alkyl (for example pyridyloxy-C₁-C₆-alkyl,pyrimidyloxy-C₁-C₆-alkyl or thiazolyloxy-C₁-C₆-alkyl),

R² preferably represents in each case optionally halogen-substitutedC₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl,poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,

represents optionally halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substitutedC₃-C₈-cycloalkyl, or

represents in each case optionally halogen-, cyano-, nitro-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- orC₁-C₆-halogenoalkoxy-substituted phenyl or benzyl,

R³ preferably represents optionally halogen-substituted C₁-C₈-alkyl orrepresents in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, cyano- ornitro-substituted phenyl or benzyl,

R⁴ and R⁵ independently of one another each preferably represent in eachcase optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio,C₂-C₈-alkenylthio, C₃-C₇-cycloalkylthio or represent in each caseoptionally halogen-, nitro-, cyano-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkyl- or C₁-C₄-halogenoalkyl-substituted phenyl, phenoxy orphenylthio,

R⁶ and R⁷ independently of one another each preferably representhydrogen, represent in each case optionally halogen-substitutedC₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, represent optionally halogen-,C₁-C₈-halogenoalkyl-, C₁-C₈-alkyl- or C₁-C₈-alkoxy-substituted phenyl,optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- orC₁-C₈-alkoxy-substituted benzyl or together with the N atom to whichthey are attached represent an optionally C₁-C₄-alkyl-substitutedC₃-C₆-alkylene radical in which optionally one carbon atom is replacedby oxygen or sulphur,

R⁸ preferably represents in each case optionally halogen-substitutedC₁-C₁₀-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkinyl, C₁-C₈-alkoxy-C₁-C₄-alkyl,C₃-C₈-alkenyloxy-C₁-C₄-alkyl, C₃-C₈-alkinyloxy-C₁-C₄-alkyl,C₁-C₈-alkylcarbonyl-C₁-C₄-alkyl, C₁-C₈-alkoxycarbonyl-C₁-C₄-alkyl,represents optionally fluorine-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted cycloalkyl or represents optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl-C₁-C₄-alkyl,phenylcarbonyl-C₁-C₄-alkyl or phenoxy-C₁-C₄-alkyl,

R⁹ preferably represents hydrogen, optionally halogen-substitutedC₁-C₁₀-alkyl, C₃-C₁₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl,C₁-C₈-alkylthio-C₁-C₈-alkyl, cycloalkyl having 3 to 8 ring atoms whichmay be interrupted by an oxygen or sulphur atom, represents phenyl,phenyl-C₁-C₆-alkyl or phenoxy-C₁-C₆-alkyl or hetaryl-C₁-C₆-alkyl havingin each case 5 or 6 ring atoms, where the ring contains 1 or 2 identicalor different oxygen, nitrogen and sulphur atoms, each of which isoptionally mono- to trisubstituted by identical or differentsubstituents from the group consisting of halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano andnitro, or

R¹⁰ preferably represents hydrogen, C₁-C₁₀-alkyl, C₃-C₁₀-alkenyl orrepresents a group CO—R¹¹, or

R⁹ and R¹⁰ together with the nitrogen atom to which they are attachedpreferably represent an optionally C₁-C₄-alkyl-substituted three- toseven-membered saturated ring in which optionally one methylene groupwhich is not directly adjacent to the nitrogen atom may be replaced byan oxygen or sulphur atom,

R¹¹ preferably represents hydrogen, in each case optionallyhalogen-substituted C₁-C₁₀-alkyl, C₃-C₁₀-alkenyl, C₁-C₁₀-alkoxy,optionally halogen-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-substitutedC₃-C₈-cycloalkyl or represents optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano- ornitro-substituted phenyl, phenyl-C₁-C₆-alkyl, benzyloxy or phenoxy,

R¹⁶ preferably represents hydrogen, represents in each case optionallyhalogen-substituted C₁-C₈-alkyl or C₁-C₈-alkoxy, represents optionallyhalogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl inwhich optionally one methylene group is replaced by oxygen or sulphur,or represents in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- orcyano-substituted phenyl, phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkoxy,

R¹⁷ preferably represents hydrogen or C₁-C₈-alkyl, or

R¹⁶ and R¹⁷ together preferably represent C₄-C₆-alkanediyl,

R¹⁸ and R¹⁹ are identical or different and each preferably representsC₁-C₆-alkyl, or

R¹⁸ and R¹⁹ together preferably represent a C₂-C₄-alkanediyl radicalwhich is optionally substituted by C₁-C₆-alkyl, C₁-C₆-halogenoalkyl orby optionally halogen-, C₁-C₆-alkyl-, C₁-C₄-halogenoalkyl-,C₁-C₆-alkoxy-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl,

R²⁰ and R²¹ independently of one another each preferably representhydrogen, represent optionally halogen-substituted C₁-C₈-alkyl orrepresent optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, or

R²⁰ and R²¹ together with the carbon atom to which they are attachedpreferably represent a carbonyl group or represent optionally halogen-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₅-C₇-cycloalkyl in whichoptionally one methylene group is replaced by oxygen or sulphur,

R²² and R²³ independently of one another each preferably representC₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₁-C₁₀-alkoxy, C₁-C₁₀-alkylamino,C₃-C₁₀-alkenylamino, di-(C₁-C₁₀-alkyl)amino or di-(C₃-C₁₀-alkenyl)amino.

In the radical definitions mentioned as being preferred, halogen,including as substituent, such as, for example, in halogenoalkyl,represents fluorine, chlorine, bromine and iodine, in particularfluorine and chlorine.

X particularly preferably represents hydrogen, fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, nitro or cyano or represents optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy orbenzyloxy,

V particularly preferably represents hydrogen, fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy,C₁-C₄-halogenoalkoxy, phenyl, nitro or cyano,

W particularly preferably represents hydrogen, fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy,C₁-C₄-halogenoalkoxy, nitro or cyano,

Y and Z independently of one another each particularly preferablyrepresent hydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy, cyano, nitro oreach represent optionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₂-halogenoalkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkoxy-, cyano- ornitro-substituted phenyl, phenoxy or benzyloxy,

X and V together with the carbon atoms to which they are attachedparticularly preferably represent an optionally fluorine-, chlorine- orC₁-C₄-alkyl-substituted 5- or 6-membered ring which may optionally beinterrupted by two not directly adjacent oxygen atoms, with the provisothat Y and Z do not form a ring,

Y and Z together with the carbon atoms to which they are attachedparticularly preferably represent an optionally fluorine-, chlorine- orC₁-C₄-alkyl-substituted 5- or 6-membered ring which may optionally beinterrupted by one or two oxygen atoms, with the proviso that X and V donot form a ring,

m particularly preferably represents the numbers 1 and 2,

with the proviso that at least one radical of the substituents V, W, X,Y or Z has to different from hydrogen,

F¹ and F² each particularly preferably represent one of the groups

A particularly preferably represents hydrogen, in each case optionallyfluorine- or chlorine-substituted C₁-C₁₀-alkyl,C₁-C₈-alkoxy-C₁-C₆-alkyl, optionally fluorine-, chlorine-, C₁-C₄-alkyl-or C₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl in which optionally onering member is replaced by oxygen or sulphur, or represents phenyl orphenyl-C₁-C₂-alkyl, each of which is optionally mono- to disubstitutedby fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₂-halogenoalkyl,C₁-C₄-alkoxy, C₁-C₂-halogenoalkoxy, cyano or nitro,

B particularly preferably represents hydrogen or C₁-C₆-alkyl, or

A, B and the carbon atom to which they are attached particularlypreferably represent saturated or unsaturated C₅-C₇-cycloalkyl in whichoptionally one ring member is replaced by oxygen or sulphur and which isoptionally monosubstituted by C₁-C₆-alkyl, C₅-C₆-cycloalkyl,C₁-C₂-halogenoalkyl, C₁-C₆-alkoxy, fluorine, chlorine or phenyl, or

A, B and the carbon atom to which they are attached particularlypreferably represent C₅-C₆-cycloalkyl which is substituted by analkylenediyl group which optionally contains one or two not directlyadjacent oxygen or sulphur atoms or by an alkylenedioxyl or by analkylenedithiol group which together with the carbon atom to which it isattached forms a further 5- or 6-membered ring, or

A, B and the carbon atom to which they are attached particularlypreferably represent C₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in which twosubstituents together with the carbon atoms to which they are attachedrepresent C₂-C₄-alkanediyl, C₂-C₄-alkenediyl in which optionally onemethylene group is replaced by oxygen or sulphur, or butadienediyl, eachof which is optionally substituted by C₁-C₅-alkyl, C₁-C₅-alkoxy,fluorine, chlorine or bromine,

D particularly preferably represents hydrogen, represents in each caseoptionally fluorine- or chlorine-substituted C₁-C₈-alkyl, C₃-C₆-alkenyl,C₁-C₆-alkoxy-C₂-C₄-alkyl or C₁-C₆-alkylthio-C₂-C₄-alkyl, representsoptionally fluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy- orC₁-C₂-halogenoalkyl-substituted C₃-C₇-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur, or represents phenylor phenyl-C₁-C₂-alkyl, each of which is optionally mono- todisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₂-halogenoalkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkoxy, cyano or nitro,or represents the group CO—R¹¹,

A and D together particularly preferably represent optionallysubstituted C₃-C₅-alkanediyl in which one methylene group may bereplaced by a carbonyl group, oxygen or sulphur, possible substituentsbeing hydroxyl, C₁-C₆-alkyl or C₁-C₄-alkoxy, or

A and D (in the case of the compounds of formula (I-1)) together withthe atoms to which they are attached particularly preferably representone of the groups AD-1 to AD-10:

A and Q¹ together particularly preferably represent C₃-C₄-alkanediyl orC₃-C₄-alkenediyl, each of which is optionally mono- or disubstituted byidentical or different substituents from the group consisting ofhydroxyl, fluorine, chlorine, by C₁-C₈-alkyl or C₁-C₄-alkoxy, each ofwhich is optionally mono- to trisubstituted by fluorine, or representsalkanedienediyl which is optionally mono- to disubstituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro or cyano, with the proviso that B and Q²together with the carbon atoms to which they are attached represent adouble bond and at least one of the substituents W or X does notrepresent hydrogen,

Q¹ particularly preferably represents hydrogen, C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl or optionallymethyl- or methoxy-substituted C₃-C₆-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur, or

Q² particularly preferably represents hydrogen or C₁-C₄-alkyl,

G particularly preferably represents hydroxyl (a) or represents one ofthe groups

 in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur,

R¹ particularly preferably represents C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl, each of which isoptionally mono- to trisubstituted by fluorine or chlorine, orrepresents optionally fluorine-, chlorine-, C₁-C₅-alkyl- orC₁-C₅-alkoxy-substituted C₃-C₆-cyclo-alkyl in which optionally one ortwo not directly adjacent ring members are replaced by oxygen and/orsulphur,

represents phenyl which is optionally mono- to disubstituted byfluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, C₁-C₂-alkylthio orC₁-C₂-alkylsulphonyl,

represents phenyl-C₁-C₄-alkyl which is optionally mono- to disubstitutedby fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₃-halogenoalkyl or C₁-C₃-halogenoalkoxy,

represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl,each of which is optionally mono- to disubstituted by fluorine,chlorine, bromine or C₁-C₄-alkyl,

R² particularly preferably represents C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl orC₁-C₆-alkoxy-C₂-C₆-alkyl, each of which is optionally mono- totrisubstituted by fluorine,

represents phenyl or benzyl, each of which is optionally mono- todisubstituted by fluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl,C₁-C₃-alkoxy, C₁-C₂-halogenoalkyl or C₁-C₂-halogenoalkoxy,

R³ particularly preferably represents C₁-C₆-alkyl which is optionallymono- to trisubstituted by fluorine, or represents phenyl which isoptionally mono- to disubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,cyano or nitro,

R⁴ and R⁵ independently of one another each particularly preferablyrepresent C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio, C₃-C₄-alkenylthio,C₃-C₆-cycloalkylthio or represent phenyl, phenoxy or phenylthio, each ofwhich is optionally mono- to disubstituted by fluorine, chlorine,bromine, nitro, cyano, C₁-C₃-alkoxy, Cl C₃-halogenoalkoxy, C₁-C₃-alkylor C₁-C₃-halogenoalkyl,

R⁶ particularly preferably represents C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, represents phenylwhich is optionally mono- to disubstituted by fluorine, chlorine,bromine, C₁-C₃-halogenoalkyl, C₁-C₄-alkyl or C₁-C₄-alkoxy, representsbenzyl which is optionally mono- to disubstituted by fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₃-halogenoalkyl or C₁-C₄-alkoxy,

R⁷ particularly preferably represents hydrogen, C₁-C₆-alkyl orC₃-C₆-alkenyl,

R⁶ and R⁷ together with the nitrogen atom to which they are attachedparticularly preferably represent a 5- or 6-membered ring in whichoptionally one methylene group which is not directly adjacent to thenitrogen atom may be replaced by an oxygen or sulphur atom and which isoptionally mono- to disubstituted by methyl or ethyl,

R⁸ particularly preferably represents C₁-C₆-alkyl, C₃-C₆-alkenyl,C₃-C₆-alkinyl, C₁-C₆-alkoxy-C₁-C₂-alkyl, C₃-C₆-alkenyloxy-C₁-C₂-alkyl,C₃-C₈-alkinyloxy-C₁-C₂-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₂-alkyl,C₁-C₆-alkoxycarbonyl-C₁-C₂-alkyl, each of which is optionally mono- totrisubstituted by fluorine or chlorine, or representsphenyl-C₁-C₂-alkyl, phenylcarbonyl-C₁-C₄-alkyl or phenoxy-C₁-C₂-alkyl,each of which is optionally mono- to disubstituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₁₀-halogenoalkoxy, cyano or nitro,

R⁹ particularly preferably represents hydrogen, represents C₁-C₆-alkyl,C₃-C₆-alkenyl or C₃-C₆-cycloalkyl, each of which is optionally mono- totrisubstituted by fluorine or chlorine, represents phenyl-C₁-C₂-alkyl orpyridyl-C₁-C₂-alkyl, each of which is optionally mono- to disubstitutedby fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, cyano or nitro,

R¹⁰ particularly preferably represents hydrogen, C₁-C₆-alkyl,C₃-C₆-alkenyl or represents a group CO—R¹¹ or

R⁹ and R¹⁰ together with the nitrogen atom to which they are attachedparticularly preferably represent a 5- or 6-membered saturated ring inwhich optionally one methylene group which is not directly adjacent tothe nitrogen atom may be replaced by an oxygen or sulphur atom and whichis optionally mono- to disubstituted by methyl or ethyl,

R¹¹ particularly preferably represents hydrogen, represents C₁-C₆-alkyl,C₃-C₆-alkenyl, C₁-C₆-alkoxy, each of which is optionally mono- totrisubstituted by fluorine or chlorine, represents C₃-C₆-cycloalkylwhich is optionally mono- to disubstituted by fluorine, chorine, methyl,ethyl, methoxy or ethoxy, or represents phenyl which is optionally mono-to disubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, cyano or nitro.

In the radical definitions mentioned as being particularly preferred,halogen, including as substituent, such as, for example, inhalogenoalkyl, represents fluorine, chlorine, bromine and iodine, inparticular fluorine, chlorine and bromine, particularly preferablyfluorine or chlorine.

V very particularly preferably represents hydrogen, fluorine, chlorine,bromine, nitro, methyl, phenyl, methoxy or trifluoromethyl,

W very particularly preferably represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, trifluoromethyl, methoxy,

X very particularly preferably represents hydrogen, bromine, fluorine,chlorine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy,n-propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy,trifluoromethoxy, nitro or cyano,

or represents phenyl, phenoxy or benzyloxy, each of which is optionallymono- to disubstituted by fluorine, chlorine, bromine, methyl,tert-butyl, trifluoromethyl, methoxy, trifluoromethoxy, nitro or cyano,

Y very particularly preferably represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, i-propyl, tert-butyl, trifluoromethyl,difluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy,difluoromethoxy, cyano, nitro or represents phenyl which is optionallymono- to disubstituted by fluorine, chlorine, bromine, methyl,trifluoromethyl, methoxy, trifluoromethoxy, cyano or nitro,

Z very particularly preferably represents hydrogen, fluorine, chlorine,bromine, methyl, trifluoromethyl, methoxy, trifluoromethoxy, cyano,nitro or represents phenyl which is optionally mono- to disubstituted byfluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy,trifluoromethoxy, cyano or nitro,

X and V together with the carbon atoms to which they are attached veryparticularly preferably represent an optionally fluorine- ormethyl-substituted 5- or 6-membered ring which is interrupted by two notdirectly adjacent oxygen atoms, with the proviso that Y and Z do notform a ring,

Y and Z together with the carbon atoms to which they are attached veryparticularly preferably represent an optionally fluorine- ormethyl-substituted 5- or 6-membered ring which may be interrupted by oneor two not directly adjacent oxygen atoms, with the proviso that X and Vdo not form a ring,

m very particularly preferably represents the number 2, with the provisothat at least one radical of the substituents V, W, X, Y or Z has to bedifferent from hydrogen,

F¹ and F² each very particularly preferably represent one of the groups

A very particularly preferably represents hydrogen, optionallyfluorine-substituted C₁-C₆-alkyl, optionally fluorine-, methyl- ormethoxy-substituted C₃-C₆-cycloalkyl or represents phenyl or benzyl,each of which is optionally mono- to disubstituted by fluorine,chlorine, bromine, methyl, iso-propyl, tert-butyl, methoxy,trifluoromethyl, trifluoromethoxy, cyano or nitro,

B very particularly preferably represents hydrogen or C₁-C₄-alkyl, or

A, B and the carbon atom to which they are attached very particularlypreferably represent saturated C₅-C₆-cycloalkyl in which optionally onering member is replaced by oxygen or sulphur and which is optionallymonosubstituted by methyl, ethyl, n-propyl, isopropyl, butyl, iso-butyl,sec-butyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, n-propoxy,iso-propoxy, n-butoxy, iso-butoxy, fluorine or chlorine, or

A, B and the carbon atom to which they are attached very particularlypreferably represent C₅-C₆-cycloalkyl in which two substituents togetherwith the carbon atoms to which they are attached representC₂-C₄-alkanediyl or C₂-C₄-alkenediyl in which in each case optionallyone methylene group is replaced by oxygen or sulphur, or representbutadienediyl,

D very particularly preferably represents hydrogen, represents in eachcase optionally fluorine- or chlorine-substituted C₁-C₆-alkyl,C₃-C₄-alkenyl, C₁-C₄-alkoxy-C₂-C₃-alkyl, C₁-C₄-alkylthio-C₂-alkyl orC₃-C₆-cycloalkyl in which optionally one methylene group is replaced byoxygen or sulphur, or represents phenyl or benzyl, each of which isoptionally mono- to disubstituted by fluorine, chlorine, bromine,methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy,trifluoromethyl, trifluoromethoxy, cyano or nitro (in compounds of theformula (I-1), D preferably represents hydrogen), or represents thegroup CO—R¹¹, or

A and D together very particularly preferably represent optionallysubstituted C₃-C₄-alkanediyl in which optionally one carbon atom isreplaced by sulphur and which is optionally substituted by methyl, or

A and D (in the case of the compounds of the formula (I-1)) togetherwith the atoms to which they are attached represent one of the groupsAD-1 to AD-10:

or

A and Q¹ together very particularly preferably representC₃-C₄-alkanediyl or butenediyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, hydroxyl, methyl or methoxy, orrepresent alkanedienediyl which is optionally mono- to disubstituted byfluorine, chlorine, bromine, methyl, methoxy, trifluoromethoxy, cyano ornitro, with the proviso that B and Q² together with the carbon atoms towhich they are attached represent a double bond and at least one of thesubstituents W or X does not represent hydrogen,

Q¹ very particularly preferably represents hydrogen, methyl,cyclopropyl, cyclopentyl or cyclohexyl,

Q² very particularly preferably represents hydrogen and methyl,

G very particularly preferably represents hydroxyl (a) or represents oneof the groups

 in particular (a), (b), (c), (g), (h) or (i) in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur,

R¹ very particularly preferably represents C₁-C₁₄-alkyl, C₂-C₁₄-alkenyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl, each of which isoptionally mono- to trisubstituted by fluorine or chlorine, orrepresents C₃-C₆-cycloalkyl in which optionally one or two not directlyadjacent ring members are replaced by oxygen and which is optionallymono- to disubstituted by fluorine, chlorine, methyl, ethyl, i-propyl,i-butyl, tert-butyl, methoxy, ethoxy or iso-propoxy,

represents phenyl which is optionally mono- to disubstituted byfluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, i-propyl,methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,

represents furanyl, thienyl or pyridyl, each of which is optionallymono- to disubstituted by fluorine, chlorine, bromine, methyl or ethyl,

R² very particularly preferably represents C₁-C₁₀-alkyl, C₂-C₁₀-alkenylor C₁-C₄-alkoxy-C₂-C₄-alkyl, each of which is optionally mono- totrisubstituted by fluorine,

or represents phenyl or benzyl, each of which is optionally mono- todisubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl,i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,

R³ very particularly preferably represents methyl, ethyl, n-propyl,isopropyl, each of which is optionally mono- to trisubstituted byfluorine, or represents phenyl which is optionally monosubstituted byfluorine, chlorine, bromine, methyl, tert-butyl, methoxy,trifluoromethyl, trifluoromethoxy, cyano or nitro,

R⁴ and R⁵ independently of one another each very particularly preferablyrepresent C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,di-(C₁-C₄-alkyl)amino, C₁-C₄-alkylthio or represent phenyl, phenoxy orphenylthio, each of which is optionally mono- to disubstituted byfluorine, chlorine, bromine, methyl, nitro, cyano, methoxy,trifluoromethoxy or trifluoromethyl,

R⁶ very particularly preferably represents C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,represents phenyl which is optionally mono- to disubstituted byfluorine, chlorine, bromine, trifluoromethyl, methyl or methoxy,represents benzyl which is optionally mono- to disubstituted byfluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy,

R⁷ very particularly preferably represents hydrogen, C₁-C₄-alkyl orC₃-C₄-alkenyl,

R⁶ and R⁷ together with the nitrogen atom to which they are attachedvery particularly preferably represent a 5- or 6-membered ring in whichoptionally one methylene group which is not directly adjacent to thenitrogen atom may be replaced by an oxygen or sulphur atom and which isoptionally mono- to disubstituted by methyl,

R⁸ very particularly preferably represents C₁-C₄-alkyl, C₃-C₄-alkenyl,C₁-C₄-alkoxy-methyl, C₃-C₄-alkenyloxy-methyl, C₃-C₄-alkinyloxy-methyl,C₁-C₄-alkylcarbonyl-methyl, C₁-C₄-alkoxycarbonyl-methyl, each of whichis optionally mono- to trisubstituted by fluorine or chlorine, orrepresents benzyl, phenylcarbonyl-methyl or phenoxy-methyl, each ofwhich is optionally mono- to disubstituted by fluorine, chlorine,bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano ornitro,

R⁹ very particularly preferably represents hydrogen, representsC₁-C₄-alkyl, allyl, cyclopropyl, cyclopentyl, cyclohexyl, each of whichis optionally mono- to trisubstituted by fluorine or chlorine,represents benzyl which is optionally mono- to disubstituted byfluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl,methoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,

R¹⁰ very particularly preferably represents hydrogen, C₁-C₄-alkyl, allylor represents a group CO—R¹¹, or

R⁹ and R¹⁰ together with the nitrogen atom to which they are attachedvery particularly preferably represent a 5- to 6-membered saturated ringin which optionally one methylene group which is not directly adjacentto the nitrogen atom may be replaced by an oxygen or sulphur atom andwhich is optionally mono- to disubstituted by methyl,

R¹¹ very particularly preferably represents hydrogen, representsC₁-C₄-alkyl, C₃-C₄-alkenyl, C₁-C₄-alkoxy, each of which is optionallymono- to trisubstituted by fluorine or chlorine, represents cyclopropyl,cyclopentyl or cyclohexyl, each of which is optionally monosubstitutedby fluorine, chlorine, methyl or methoxy, or represents phenyl which isoptionally mono- to disubstituted by fluorine, chlorine, bromine,methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro.

Particular emphasis is given to compounds of the formula (I) in which

V represents hydrogen, fluorine, chlorine, bromine, methyl,trifluoromethyl, nitro or phenyl,

W represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,

X represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,n-propyl, isopropyl, ethoxy, n-propoxy, iso-propoxy, methoxy,trifluoromethyl, nitro or cyano,

Y represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, difluoromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy or phenyl,

Z represents hydrogen, fluorine, chlorine, bromine, methyl,trifluoromethyl,

Y and Z together with the carbon atoms to which they are attached form a5-membered ring which may be interrupted by one or two not directlyadjacent oxygen atoms, with the proviso that X and V do not form a ring,

m represents 2, with the proviso that at least one radical of thesubstituents V, W, X, Y or Z has to be different from hydrogen,

F¹ and F² each represent one of the groups

 in which

A represents hydrogen, C₁-C₄-alkyl, represents phenyl or benzyl, each ofwhich is optionally mono- to disubstituted by chlorine or fluorine,

B represents hydrogen or C₁-C₄-alkyl,

A and B and the carbon atom to which they are attached representsaturated cyclohexyl in which optionally one ring member is replaced byoxygen and which is optionally monosubstituted by methyl, ethyl,n-propyl, isopropyl, butyl, iso-butyl, sec-butyl, tert-butyl,trifluoromethyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy,iso-butoxy, fluorine or chlorine,

D represents hydrogen, C₁-C₄-alkyl, represents phenyl or benzyl, each ofwhich is optionally mono- or disubstituted by chlorine, fluorine,bromine, or represents a group CO—R¹¹,

A and Q¹ together represent C₃-C₄-alkanediyl or butenediyl, each ofwhich is optionally mono- or disubstituted by methyl, fluorine orchlorine, or represent alkanedienediyl which is optionally mono- ordisubstituted by methyl or chlorine,

with the proviso that B and Q² together with the carbon atoms to whichthey are attached represent a double bond and at least one of thesubstituents W or X does not represent hydrogen,

G represents hydroxyl (a) or represents

R¹ represents C₁-C₈-alkyl,

R² represents C₁-C₈-alkyl,

L and M each represent oxygen,

R⁹ represents hydrogen,

R¹⁰ represents hydrogen or represents a group CO—R¹¹,

R¹¹ represents C₁-C₄-alkyl.

Particular preference is given to compounds of the formula (I-1) inwhich D represents hydrogen, in which the substituent G represents theradicals (a), (b), (g), (h) or (i) and in which A, B, V, W, X, Y, Z, R¹,R², R⁶, R⁷, R⁸, R⁹, R¹⁰ and m have the meanings listed in the veryparticularly preferred ranges.

Particular preference is given to compounds of the formula (I-2) inwhich D represents hydrogen, in which the substituent G represents theradicals (a), (b), (g), (h) or (i) and in which A, B, V, W, X, Y, Z, R¹,R², R⁶, R⁷, R⁸, R⁹, R¹⁰ and m have the meanings listed in the veryparticularly preferred ranges.

Particular preference is given to compounds of the formula (I-3) inwhich D represents hydrogen, in which the substituents A and Q¹ eachrepresent an optionally substituted alkanedienediyl radical, possiblesubstituents being the radicals mentioned in the particularly preferredrange, in which the substituent G represents the radicals (a), (b), (g),(h) or (i) and in which B, Q², V, W, X, Y, Z, R¹, R², R⁶, R⁷, R⁸, R⁹,R¹⁰ and m have the meanings listed in the very particularly preferredranges.

The abovementioned general or preferred radical definitions can becombined with one another as desired, i.e. including combinationsbetween the respective ranges and preferred ranges. They apply both tothe end products and, correspondingly, to the precursors andintermediates.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (preferably).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Particular preference is given to compounds of the formula (I) in whichG represents hydrogen.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched as far as this ispossible, including in combination with heteroatoms, such as, forexample, in alkoxy.

Unless stated otherwise, optionally substituted radicals can be mono- orpolysubstituted, where in the case of polysubstitution the substituentscan be identical or different.

Using, according to process (A), ethyl2{[(4-chlorobenzyl)sulphonyl]amino}-2-methylpropanoate as startingmaterial, the course of the process according to the invention can berepresented by the following reaction scheme:

Using, according to process (B), ethyl2-{[(2,6-dichlorobenzyl)sulphonyl]oxy}-2-methylpropanoate, the course ofthe process according to the invention can be represented by thefollowing reaction scheme:

Using, according to process (C), ethyl2-[(2,4-dichlorobenzyl)sulphonyl]benzoate, the course of the processaccording to the invention can be represented by the following reactionscheme:

Using, according to process (D), for example, ethyl2-[(4-nitrobenzyl)sulphonyl]-tetrahydro-1(2H)-pyridazinecarboxylate asstarting material, the course of the process according to the inventioncan be represented by the following reaction scheme:

Using, according to process (E, variant α),5-(2-chlorophenyl)-4-hydroxy-3,3-dimethyl-2,3-dihydro-1H-1-isothiazole-1,1-dioneand pivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the following reactionscheme:

Using, according to process (E, variant β),4-hydroxy-5,5-dimethyl-3-[3-(trifluoromethyl)phenyl]-1,2[lambda]⁶-oxathiole-2,2(5H)-dioneand acetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the following reactionscheme:

Using, according to process (F),3-hydroxy-2-(4-nitrophenyl)-1H-1-benzothiophene-1,1-dione andethoxyethyl chloroformate as starting materials, the course of theprocess according to the invention can be represented by the followingreaction scheme:

Using, according to process (G),5-(3-chlorophenyl)-4-hydroxy-3,3-dimethyl-2,3-dihydro-1H-1-isothiazole-1,1-dioneand methyl chloromonothioformate as starting materials, the course ofthe reaction can be represented as follows:

Using, according to process (H),3-(3-chloro-4-trifluoromethylphenyl)-4-hydroxy-2-thia-1-azaspiro[4.5]dec-3,4-ene-2,2-dioneand methanesulphonyl chloride as starting materials, the course of thereaction can be represented by the following reaction scheme:

Using, according to process (I),3-(3,4-dichlorophenyl)-4-hydroxy-5,5-dimethyl-1,2-oxathiole-2,2(5H)-dioneand 2,2,2-trifluoroethyl methanethiophosphonyl chloride as startingmaterials, the course of the reaction can be represented by thefollowing reaction scheme:

Using, according to process (J),4-hydroxy-3,3-dimethyl-5-[2-(trifluoromethyl)-phenyl]-2,3-dihydro-1H-1-isothiazole-1,1-dioneand NaOH as components, the course of the process according to theinvention can be represented by the following reaction scheme:

Using, according to process (K, variant α),3-(4-chlorophenyl)-4-hydroxy-1-oxa-2-thiaspiro[4.4]non-3,4-ene-2,2-dioneand ethyl isocyanate as starting materials, the course of the reactioncan be represented by the following reaction scheme:

Using, according to process (K, variant β),5-(2-chlorophenyl)-4-hydroxy-3-methyl-2,3-dihydro-1H-1-isothiazole-1,1-dioneand dimethylcarbamoyl chloride as starting materials, the course of thereaction can be represented by the following scheme:

Using, according to process (L),3-(2-fluorophenyl)-4-hydroxy-1-oxa-2-thiaspiro[4.5]dec-3,4-ene-2,2-dioneand dimethyl sulphate as starting materials, the course of the reactioncan be represented by the following reaction scheme:

Using, according to process (M, variant α),5-(4-chlorophenyl)-4-hydroxy-2-isopropyl-2,3-dihydro-1H-1-isothiazole-1,1-dione,methylamine and acetic acid as starting materials, the course of thereaction of the process according to the invention can be represented bythe following reaction scheme:

Using, according to process (M, variant β),N-(1-cyano-1-methylethyl)-(2,4-dichlorophenyl)methanesulphonamide andpotassium tert-butoxide as starting materials, the course of thereaction of the process according to the invention can be represented bythe following reaction scheme:

Using, according to process (N, variant α),4-amino-5-[3-chloro-4-(trifluoromethyl)phenyl]-3,3-dimethyl-2,3-dihydro-1H-1-isothiazole-1,1-dioneand propionyl chloride as starting materials, the course of the reactionof the process according to the invention can be represented by thefollowing reaction scheme:

Using, according to process (N, variant β),4-amino-3,3-dimethyl-5-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-1-isothiazole-1,1-dioneand acetic anhydride as starting materials, the course of the reactionof the process according to the invention can be represented by thefollowing reaction scheme:

Using, according to process (N, variant γ),4-amino-2-benzyl-5-(4-fluorophenyl)-3,3-dimethyl-2,3-dihydro-1H-1-isothiazole-1,1-dioneand methyl orthoformate as starting materials, the course of thereaction of the process according to the invention can be described bythe following reaction scheme:

Using, according to process (O),4-amino-3,3-dimethyl-5-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-1-isothiazole-1,1-dioneand acetyl chloride as starting materials and sodium hydride as base,the course of the reaction of the process according to the invention canbe represented by the following reaction scheme:

The compounds of the formula (II)

in which A, B, D, V, W, X, Y, Z, R¹² and m are each as defined above

and which are required as starting materials in the process (A)according to the invention

are novel.

The amino acid esters of the formula (II) are obtained, for example,when amino acid derivatives of the formula (XXII)

in which

A, B, R¹² and D are each as defined above

are reacted with substituted benzyl-S(O)_(m) halides of the formula(XXIII)

in which

V, W, X, Y, Z and m are each as defined above and

Hal represents chlorine or bromine, in particular chlorine

(H.-D. Stachel, G. Drasch, Arch. Pharm. 318, 304 (1985)),

or when amino acids of the formula (XXIV)

in which

A, B, D, V, W, X, Y, Z and m are each as defined above

are esterified (Chem. Ind. (London) 1568 (1968)).

The compounds of the formula (XXIV)

in which

A, B, D, V, W, X, Y, Z and m are each as defined above

are novel.

The compounds of the formula (XXIV) are obtained when amino acids of theformula (XXV)

in which

A, B and D are each as defined above

are acylated with substituted benzyl-S(O)_(m) halides of the formula(XXIII)

in which

V, W, X, Y, Z and m are each as defined above and

Hal represents chlorine or bromine, in particular chlorine,

for example according to Schotten-Baumann (Organikum, VEB DeutscherVerlag der Wissenschaften, Berlin 1977, p. 505).

Some of the compounds of the formula (XXIII) are novel. They can beprepared by processes known in principle.

The compounds of the formula (XXIII) in which V, W, X, Y and Z are asdefined above and m represents the number 2 are obtained, for example,by converting substituted benzyl halides of the formula (XXXIII)

in which

V, W, X, Y and Z are each as defined above and

Hal represents chlorine or bromine

with thiourea into the isothiuronium salts of the formula (XXVI-A)

in which

V, W, X, Y and Z are each as defined above and

Hal represents chlorine or bromine

and cleaving them oxidatively using chlorine (B. Johnson J. M. Sprague,J. Am. Chem. Soc. 58, 1348 (1936))

or by converting benzyl halides of the formula (XXXIII) with sodiumsulphite into the sodium salts of the corresponding benzylsulphonicacids of the formula (XXVI-B)

in which

V, W, X, Y and Z are each as defined above

and reacting these with phosphorus pentachloride (W. V. Farrar, J. Chem.Soc. 1960, 3063; Ruggli, Helv. Chim. Acta 14 (1931), 541).

Some of the compounds of the formulae (XXIII) and (XXVI) are known,and/or they can be prepared by known processes (see, for example,Compagnon, Miocque Ann. Chim. (Paris) [14] 5, pp. 11-22, 23-27 (1970)).

The substituted cyclic aminocarboxylic acids of the formula (XXII) inwhich A and B form a ring are, in general, obtainable by theBucherer-Bergs synthesis or by the Strecker synthesis, and they are ineach case obtained in different isomeric forms. Thus, under theconditions of the Bucherer-Bergs synthesis, what is obtained arepredominantly those isomers (hereinbelow for the sake of simplicityreferred to as β) in which the radicals R and the carboxyl group are inan equatorial position, whereas the conditions of the Strecker synthesisyield predominantly those isomers (hereinbelow for the sake ofsimplicity referred to as α) where the amino group and the radicals Rare in an equatorial position.

(L. Munday, J. Chem. Soc. 4372 (1961); J. T. Eward, C. Jitrangeri, Can.J. Chem. 53, 3339 (1975).

Furthermore, the starting materials of the formula (I)

in which

A, B, D, V, W, X, Y, Z, R¹² and m are each as defined above

and which are used for the process (A) above can be prepared byconverting aminonitriles of the formula (XXVII)

in which

A, B and D are each as defined above

with substituted benzyl-S(O)_(m) halides of the formula (XXIII)

in which

V, W, X, Y, Z, m and Hal are each as defined above

into compounds of the formula (XXVIII)

in which

A, B, D, V, W, X, Y, Z and m are each as defined above,

and then subjecting these to an acidic alcoholysis.

The compounds of the formula (XXVIII) are likewise novel.

The compounds of the formula (III)

in which

A, B, V, W, X, Y, Z, R¹² and m are each as defined above

and which are required as starting materials for the process (B)according to the invention

are novel.

They can be prepared by methods known in principle.

Thus, the compounds of the formula (III) are obtained, for example, when

2-hydroxycarboxylic esters of the formula (XXIX)

in which

A, B and R¹² are each as defined above

are reacted with substituted benzyl-S(O)_(m) halides of the formula(XXIII)

in which

V, W, X, Y, Z, m and Hal are each as defined above

(H.-D. Stachel, G. Drasch, Arch. Pharm. 318, 304 (1985)).

The compounds of the formula (IV)

in which

A, B, Q¹, Q², V, W, X, Y, Z, m and R¹² are each as defined above

and which are required as starting materials for the process (C) aboveare novel.

They can be prepared by methods known in principle.

The 5-aryl-S(O)_(m)-carboxylic esters of the formula (IV) are obtained,for example, when 5-aryl-S(O)_(m)-carboxylic acids of the formula (XXX)

in which

V, W, X, Y, Z, A, B, Q¹, Q² and m are each as defined above

are esterified (cf. J. G. Rombardino, E. H. Wiseman, 13, 206 (1970); A.Abdel-Wahab et al., Phosphorus, Sulfur and Silicon 59, 149 (1991)) (seealso the Preparation Examples).

Furthermore, compounds of the formula (IV)

in which

A, B, Q¹, Q², V, W, X, Y, Z and R¹² are each as defined above and

m represents the numbers 1 and 2

are obtained when benzyl thioethers of the formula (XXXI)

in which

A, B, Q¹, Q², V, W, X, Y, Z and R¹² are each as defined above

are oxidized using oxidizing agents such as, for example, peracids,hydrogen peroxide, peroxides or chlorine (see Preparation Examples).

Some of the compounds of the formula (XXXI) are novel, and they can beprepared by processes known per se.

Thus, for example, compounds of the formula (XXXI)

in which

A, B, Q¹, Q², V, W, X, Y, Z and R¹² are each as defined above

are obtained when mercapto compounds of the formula (XXXII)

in which

A, B, Q¹, Q² and R¹² are each as defined above

are reacted with benzyl halides of the formula (XXXIII)

in which

V, W, X, Y and Z are each as defined above and

Hal represents chlorine or bromine

in the presence of an acid binder and in the presence of a solvent (seePreparation Examples, variant 1).

Compounds of the formula (XXXI)

in which

A, Q¹, V, W, X, Y, Z and R¹² are each as defined above

are obtained when compounds of the formula (a)

in which

A, Q¹ and R¹² are each as defined above

are reacted with compounds of the formula (b)

in which

V, W, X, Y and Z are each as defined above

in the presence of an acid and a solvent (see Preparation Examples,variant 2).

The compounds of the formula (V)

in which

A, D, V, W, X, Y, Z, m and R¹² are each as defined above

and which are required as starting materials for the process (D)according to the invention

are novel.

The hydroxides of the formula (V) are obtained, for example, whencarbamates of the formula (XXXIV)

in which

A and D are each as defined above

are reacted with substituted benzyl-S(O)_(m) halides of the formula(XXII)

in which

V, W, X, Y, Z, m and Hal are each as defined above.

The compounds of the formula (XVIII)

in which

V, W, X, Y, Z and m are each as defined above and

F¹ and F² represent the groups

in which the radicals A, B, D, Q¹ and Q² are each as defined above,

which compounds are required as starting materials for the process M (β)according to the invention,

are novel.

The nitrites of the formula (XVIII) are obtained when, for the group(1′), for example, aminonitriles of the formula (XXVII)

in which

A, B and D are each as defined above

are reacted with substituted benzyl-S(O)_(m) halides of the formula(XXIII)

in which

V, W, X, Y, Z, m and Hal are each as defined above

(S. T. Ingate, Tetrahedron 53, 17795 (1997)).

Analogously, nitriles of the formula (XVIII) for the group (2′) areobtained when, for example, cyanohydrines of the formula (XXXV)

in which

A and B are each as defined above

are reacted with substituted benzyl-S(O)_(m) halides of the formula(XXIII) in which V, W, X, Y, Z, m and Hal are each as defined above

(S. T. Ingate, Tetrahedron 53, 17795 (1997)).

Furthermore, compounds of the formula (XVIII) for the group (3′)

in which

A, B, Q¹, Q², V, W, X, Y and Z are each as defined above and

m represents the numbers 1 and 2

are obtained when benzyl thioethers of the formula (XXXVI)

in which

A, B, Q¹, Q², V, W, X, Y and Z are each as defined above

are oxidized using oxidizing agents such as, for example, peracids,hydrogen peroxide, peroxides or chlorine (see Preparation Examples, J.R. Beck, J. Heterocyclic Chem. 15, 513 (1978)).

Some of the compounds of the formula (XXXVI) are novel, and they can beprepared by known processes.

Thus, for example, compounds of the formula (XXXVI)

in which

A, B, Q¹, Q², V, W, X, Y and Z are each as defined above

are obtained when mercaptocyano compounds of the formula (XXXVII)

in which

A, B, Q¹, Q² and R¹² are each as defined above

are reacted with benzyl halides of the formula (XXXIII)

in which

V, W, X, Y and Z are each as defined above and

Hal represents chlorine or bromine

in the presence of an acid binder and in the presence of a solvent, oraccording to the process described by J. R. Beck, J. Heterocyclic Chem.15 513 (1978), or according to the Preparation Examples.

The acid halides of the formulae (VI) and (XIX), carboxylic anhydridesof the formulae (VII) and (XX), chloroformic esters or chloroformicthioesters of the formula (VIII), chloromonothioformic esters orchlorodithioformic esters of the formula (IX), sulphonyl chlorides ofthe formula (X), phosphorus compounds of the formula (XI) and metalhydroxides, metal alkoxides or amines of the formulae (XII) and (XIII)and isocyanates of the formula (XIV) and carbamoyl chlorides of theformula (XV), alkylating agents of the formula (XVI) and amines of thegeneral formula (XVII) which are furthermore required as startingmaterials for carrying out the processes (E), (F), (G), (H), (I), (J),(K), (L), (M), (N) and (O) according to the invention are generallyknown compounds of organic or inorganic chemistry.

The process (A) is characterized in that compounds of the formula (II)in which A, B, D, V, W, X, Y, Z, m and R¹² are each as defined above aresubjected to an intramolecular condensation in the presence of a base.

Diluents which are suitable for use in the process (A) according to theinvention are all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide, dimethylacetamide andN-methyl-pyrrolidine, and also alcohols, such as methanol, ethanol,propanol, isopropanol, butanol, iso-butanol and tert-butanol.

Bases (deprotonating agents) which are suitable for carrying out theprocess (A) according to the invention are all customary protonacceptors. Preference is given to using alkali metal and alkaline earthmetal oxides, hydroxides and carbonates, such as sodium hydroxide,potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate,potassium carbonate and calcium carbonate, which can also be employed inthe presence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). It is furthermore possible to usealkali metals, such as sodium or potassium. Moreover, use can be made ofalkali metal and alkaline earth metal amides and hydrides, such assodium amide, sodium hydride and calcium hydride, and furthermore alsoalkali metal alkoxides, such as sodium methoxide, sodium ethoxide andpotassium tert-butoxide. It is furthermore possible to use, for example,tertiary amines, such as triethylamine, pyridine, diazabicyclooctane(DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN) and Hünigbase.

When carrying out the process (A) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between 0° C. and250° C., preferably between 20° C. and 150° C.

The process (A) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (A) according to the invention, thereaction components of the formula (II) and the deprotonating bases aregenerally employed in twice the equimolar amount. However, it is alsopossible to use a relatively large excess (up to 3 mol) of one or theother component.

The process (B) is characterized in that compounds of the formula (III)in which A, B, V, W, X, Y, Z, m and R¹² are each as defined above aresubjected to an intramolecular condensation in the presence of a diluentand in the presence of a base.

Diluents suitable for use in the process (B) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone. Itis furthermore possible to use alcohols, such as methanol, ethanol,propanol, iso-propanol, butanol, iso-butanol and tert-butanol.

Bases (deprotonating agents) suitable for carrying out the process (B)according to the invention are all customary proton acceptors.Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which can also be employed in thepresence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). Furthermore, it is possible to usealkali metals, such as sodium or potassium. Moreover, is it possible touse alkali metal and alkaline earth metal amides and hydrides, such assodium amide, sodium hydride and calcium hydride, and furthermore alsoalkali metal alkoxides, such as sodium methoxide, sodium ethoxide andpotassium tert-butoxide. It is furthermore possible to use, for example,tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBN andHünig base.

When carrying out the process (B) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between 0° C. and250° C., preferably between 20° C. and 150° C.

The process (B) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (B) according to the invention, thereaction components of the formula (III) and the deprotonating bases aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of one orthe other component.

The process (C) is characterized in that compounds of the formula (IV)in which A, B, Q¹, Q², V, W, X, Y, Z, m and R¹² are each as definedabove are subjected to an intramolecular condensation in the presence ofa base.

Diluents suitable for use in the process (C) according to the inventionare all organic solvents which are inert to the reactants. Preference isgiven to using hydrocarbons, such as toluene and xylene, furthermoreethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethylether and diglycol dimethyl ether, moreover polar solvents, such asdimethyl sulphoxide, sulpholane, dimethylformamide, dimethylacetamideand N-methyl-pyrrolidone. It is furthermore possible to use alcohols,such as methanol, ethanol, propanol, iso-propanol, butanol, isobutanol,tert-butanol.

Suitable bases (deprotonating agents) for carrying out the process (C)according to the invention are all customary proton acceptors.Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which can also be employed in thepresence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(tris-(methoxyethoxyethyl)-amine). It is furthermore possible to usealkali metals, such as sodium or potassium. Moreover, it is possible touse alkali metal and alkaline earth metal amides and hydrides, such assodium amide, sodium hydride and calcium hydride, and furthermore alsoalkali metal alkoxides, such as sodium methoxide, sodium ethoxide andpotassium tert-butoxide. It is furthermore possible to use tert-amines,such as, for example, triethylamine, pyridine, DABCO, DBU, DBN and Hünigbase.

When carrying out the process (C) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −75° C. and250° C., preferably between 0° C. and 150° C.

The process (C) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (C) according to the invention, thereaction components of the formula (IV) and the deprotonating bases aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of one orthe other component.

The process (D) is characterized in that compounds of the formula (V) inwhich A, D, V, W, X, Y, Z, m and R¹² are each as defined above aresubject to an intramolecular condensation in the presence of bases.

Diluents suitable for use in the process (D) according to the inventionare all organic solvents which are inert to the reactants. Preference isgiven to using hydrocarbons, such as toluene and xylene, furthermoreethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethylether and diglycol dimethyl ether, moreover polar solvents, such asdimethyl sulphoxide, sulpholane, dimethylformamide, dimethylacetamideand N-methyl-pyrrolidone. It is furthermore possible to use alcohols,such as methanol, ethanol, propanol, iso-propanol, butanol, isobutanol,tert-butanol.

Bases (deprotonating agents) suitable for carrying out the process (D)according to the invention are all customary proton acceptors.

Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which can also be employed in thepresence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(tris-(methoxyethoxyethyl)-amine). It is furthermore possible to usealkali metals, such as sodium or potassium. Moreover, it is possible touse alkali metal and alkaline earth metal amides and hydrides, such assodium amide, sodium hydride and calcium hydride, and furthermore alsoalkali metal alkoxides, such as sodium methoxide, sodium ethoxide andpotassium tert-butoxide. It is furthermore possible to use, for example,tert-amines, such as triethylamine, pyridine, DABCO, DBU, DBN and Hünigbase.

When carrying out the process (D) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

The process (D) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (D) according to the invention, thereaction components of the formula (V) and the deprotonating bases aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of one orthe other component.

The process (E-α) is characterized in that compounds of the formulae(I-1-a) to (I-4-a) are in each case reacted with carbonyl halides of theformula (VI), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

Diluents suitable for use in the process (E-α) according to theinvention are all solvents which are inert to the acid halides.Preference is given to using hydrocarbons, such as benzine, benzene,toluene, xylene and tetraline, furthermore halogenated hydrocarbons,such as methylene chloride, chloroform, carbon tetrachloride,chlorobenzene and o-dichlorobenzene, moreover ketones, such as acetoneand methyl isopropyl ketone, furthermore ethers, such as diethyl ether,tetrabydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such as dimethylsulphoxide and sulpholane. The hydrolytic stability of the acid halidepermitting, the reaction can also be carried out in the presence ofwater.

Suitable acid binders for the reaction by the process (E-α) according tothe invention are all customary acid acceptors. Preference is given tousing tertiary amines, such as triethylamine, pyridine,N,N-dimethylaminopyridine (DMAP), diazabicyclooctane (DABCO),diazabicycloundecene (DBU), diazabicyclononene (DBN), Hünig base andN,N-dimethyl-aniline, furthermore alkali earth metal oxides, such asmagnesium oxide and calcium oxide, moreover alkali metal and alkalineearth metal carbonates, such as sodium carbonate, potassium carbonateand calcium carbonate, and also alkali metal hydroxides, such as sodiumhydroxide and potassium hydroxide.

When carrying out the process (E-α) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −20° C. and+150° C., preferably between 0° C. and 100° C.

When carrying out the process (E-α) according to the invention, thestarting materials of the formulae (I-1-a) to (I-4-a) and the carbonylhalide of the formula (VI) are generally each employed in approximatelyequivalent amounts. However, it is also possible to use a relativelylarge excess (up to 5 mol) of the carbonyl halide. Work-up is carriedout by customary methods.

The process (E-β) is characterized in that compounds of the formulae(I-1-a) to (I-4-a) are reacted with carboxylic anhydrides of the formula(VII), if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder.

Diluents which can be used in the process (E-β) are preferably thosediluents which are also preferred when using acid halides. Otherwise, itis also possible for carboxylic anhydride employed in excess to actsimultaneously as diluent.

Preferred acid binders which are added, if appropriate, in the process(E-β) are those acid binders which are also preferred when using acidhalides.

When carrying out the process (E-β) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −20° C. and+150° C., preferably between 0° C. and 100° C.

When carrying out the process (E-β) according to the invention, thestarting materials of the formulae (I-1-a) to (I-4-a) and the carboxylicanhydride of the formula (VII) are generally each employed inapproximately equivalent amounts. However, it is also possible to use arelatively large excess (up to 5 mol) of carboxylic anhydride. Work-upis carried out by customary methods.

In general, the diluent and excess carboxylic anhydride and thecarboxylic acid that is formed are removed by distillation or by washingwith an organic solvent or with water.

The process (F) is characterized in that compounds of the formulae(I-1-a) to (I-4-a) are in each case reacted with chloroformic esters orchloroformic thiolesters of the formula (VIII), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

Suitable acid binders for the reaction according to the process (F)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,DABCO, DBU, DBN, Hünig base and N,N-dimethyl-aniline, furthermorealkaline earth metal oxides, such as magnesium oxide and calcium oxide,moreover alkali metal and alkaline earth metal carbonates, such assodium carbonate, potassium carbonate and calcium carbonate, and alsoalkali metal hydroxides, such as sodium hydroxide and potassiumhydroxide.

Diluents suitable for use in the process (F) according to the inventionare all solvents which are inert to the chloroformic esters orchloroformic thioesters. Preference is given to using hydrocarbons, suchas benzine, benzene, toluene, xylene and tetraline, furthermorehalogenated hydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, and additionally carboxylicesters, such as ethyl acetate, and also strongly polar solvents, such asdimethyl sulphoxide and sulpholane.

When carrying out the process (F) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ifthe process is carried out in the presence of a diluent and an acidbinder, the reaction temperatures are generally between −20° C. and+100° C., preferably between 0° C. and 50° C.

The process (F) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (F) according to the invention, thestarting materials of the formulae (I-1-a) to (I-4-a) and theappropriate chloroformic ester or chloroformic thioester of the formula(VIII) are generally each employed in approximately equivalent amounts.However, it is also possible to use a relatively large excess (up to 2mol) of one or the other component. Work-up is carried out by customarymethods. In general, precipitated salts are removed and the reactionmixture that remains is concentrated by stripping off the diluent.

The process (G) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-4-a) are in each case reactedwith compounds of the formula (IX) in the presence of a diluent and, ifappropriate, in the presence of an acid binder.

In the preparation process (G), about 1 mol of chloromonothioformicester or chlorodithioformic ester of the formula (IX) is employed permole of the starting material of the formulae (I-1-a) to (I-4-a), atfrom 0 to 120° C., preferably from 20 to 60° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, esters, amides, sulphones,sulphoxides, and also halogenated alkanes.

Preference is given to using dimethylsulphoxide, ethyl acetate,tetrahydrofuran, dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-4-a) is prepared by addition of strong deprotonating agents, suchas, for example, sodium hydride or potassium tertiary-butoxide, theaddition of further acid binders can be dispensed with.

If acid binders are used, these are customary inorganic or organicbases, sodium hydroxide, sodium carbonate, potassium carbonate, pyridineand triethylamine being mentioned by way of example.

The reaction can be carried out under atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods.

The process (H) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-4-a) are in each case reactedwith sulphonyl chlorides of the formula (X), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In the preparation process (H), about 1 mol of sulphonyl chloride of theformula (X) is employed per mole of the starting material of the formula(I-1-a) to (I-8-a), at from −20 to 150° C., preferably from 20 to 70° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, nitrites, sulphones,sulphoxides or halogenated hydrocarbons, such as methylene chloride.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide, methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-4-a) is prepared by addition of strong deprotonating agents (suchas, for example, sodium hydride or potassium tertiary-butoxide), theaddition of further acid binders can be dispensed with.

If acid binders are used, these are customary inorganic or organicbases, sodium hydroxide, sodium carbonate, potassium carbonate, pyridineand triethylamine being mentioned by way of example.

The reaction can be carried out under atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods.

The process (I) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-4-a) are in each case reactedwith phosphorus compounds of the formula (XI), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In the preparation process (I), to obtain compounds of the formulae(I-1-e) to (I-4-e), from 1 to 2, preferably from 1 to 1.3, mol of thephosphorus compound of the formula (XI) are employed per mole of thecompounds (I-1-a) to (I-4-a), at temperatures between −40° C. and 150°C., preferably between −10 and 110° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, esters, amides, nitrites, alcohols,sulphides, sulphones, sulphoxides, etc.

Preference is given to using acetonitrile, dimethyl sulphoxide, ethylacetate, tetrahydrofuran, dimethylformamide, methylene chloride.

Acid binders, which are added, if appropriate, are customary inorganicor organic bases, such as hydroxides, carbonates or amines. Sodiumhydroxide, sodium carbonate, potassium carbonate, pyridine andtriethylamine may be mentioned by way of example.

The reaction can be carried out under atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods of organicchemistry. Purification of the end products obtained is preferablycarried out by crystallization, chromatographic purification orso-called “incipient distillation”, i.e. removal of the volatilecomponents under reduced pressure.

The process (J) is characterized in that compounds of the formulae(I-1-a) to (I-4-a) are reacted with metal hydroxides or metal alkoxidesof the formula (XII) or amines of the formula (XIII), if appropriate inthe presence of a diluent.

Preferred diluents for use in the process (J) according to the inventionare ethers, such as tetrahydrofuran, dioxane, diethyl ether, or elsealcohols, such as methanol, ethanol, isopropanol, and also water.

The process (J) according to the invention is generally carried outunder atmospheric pressure.

The reaction temperatures are generally between −20° C. and 100° C.,preferably between 0° C. and 50° C.

The process (K) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-4-a) are in each case reactedwith (K-α) compounds of the formula (XIV), if appropriate in thepresence of a diluent and if appropriate in the presence of a catalyst,or (K-β) with compounds of the formula (XV), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In the preparation process (K-α), about 1 mol of isocyanate of theformula (XIV) is employed per mole of the starting of the formulae(I-1-a) to (I-4-a), at from 0 to 100° C., preferably from 20 to 50° C.

Suitable diluents which are added, if appropriate, are all inert organicsolvents, such as ethers, amides, nitrites, sulphones, sulphoxides.

If appropriate, catalysts may be added to accelerate the reaction.Particularly advantageous catalysts are organotin compounds, such as,for example, dibutyltin dilaurate. The process is preferably carried outunder atmospheric pressure.

In the preparation process (K-β), about 1 mol of carbamoyl chloride orthiocarbamoyl chloride of the formula (XV) is employed per mole of thestarting material of the formulae (I-1-a) to (I-4-a), at from −20 to150° C., preferably from 0 to 70° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, esters, amides, sulphones, sulphoxidesor halogenated hydrocarbons.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran, ethylacetate, dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compound (I-1-a)to (I-4-a) is prepared by addition of strong deprotonating agents (suchas, for example, sodium hydride or potassium tertiary-butoxide), theaddition of further acid binders can be dispensed with.

If acid binders are used, these are customary inorganic or organicbases, sodium hydroxide, sodium carbonate, potassium carbonate,triethylamine or pyridine being mentioned by way of example.

The reaction can be carried out under atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods.

The process (L) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-4-a) are in each case reactedwith alkylating agents of the formula (XVI), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

Suitable diluents for carrying out the process (L) according to theinvention for preparing the compounds according to the invention areinert organic solvents. Preference is given to using aliphatic,alicyclic or aromatic, optionally halogenated hydrocarbons, such as, forexample, benzine, benzene, toluene, xylene, pentane, hexane, heptane,cyclohexane, petroleum ether, ligroin, methylene chloride, chloroform,carbon tetrachloride, chlorobenzene or dichlorobenzene, ethers, such asdiethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethyleneglycol diethyl ether or ethylene glycol dimethyl ether, ketones, such asacetone, butanone, methyl isopropyl ketone or methyl isobutyl ketone,esters, such as ethyl acetate, acids, such as acetic acid, nitriles,such as acetonitrile or propionitrile, amides, such asdimethylformamide, dimethylacetamide, N-methylpyrrolidone orhexamethylphosphoric triamide. If compounds of the formula (XVI) inliquid form are employed as reactants, it is also possible to use them,in an appropriate excess, simultaneously as diluents.

Suitable acid binders are all inorganic or organic bases which arecustomarily used. Preference is given to using alkali metal hydrides,hydroxides, amides, carbonates or bicarbonates, such as, for example,sodium hydride, sodium amide, sodium hydroxide, potassium carbonate orsodium bicarbonate, or else tertiary amines, such as, for example,triethylamine, N,N-dimethylaniline, pyridine,4-(N,N-dimethylamino)-pyridine, diazabicyclooctane (DABCO),diazabicyclononene (DBU) or Hünig base.

When carrying out the process, the reaction temperatures can be variedwithin a relatively wide range. In general, the process is carried outat between −20° C. and +200° C., preferably between 0° C. and +150° C.

For carrying out the process (L) according to the invention forpreparing the compounds according to the invention, generally in eachcase from 1 to 20 mol, preferably in each case from 1 to 5 mol, ofalkylating agent of the formula (XVI) and, if appropriate, from 1 to 5mol, preferably from 1 to 2 mol, of acid binder are employed per mole ofthe compounds of the formulae (I-1-a) to (I-4-a). The practice of thereaction and the work-up and isolation of the reaction products arecarried out by customary methods (cf. also the Preparation Examples).

The process (M-α) is characterized in that compounds of the formulae(I-1-a) to (I-4-a) are in each case reacted with amines of the formula(XVII), if appropriate in the presence of a diluent and if appropriatein the presence of an acid catalyst and a dehydrating agent.

Preferred diluents for carrying out the process (M-α) according to theinvention are inert organic solvents. These include, in particular,aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons,such as, for example, benzine, ligroin, benzene, toluene, xylene,chlorobenzene, petroleum ether, pentane, hexane, heptane, cyclohexane,dichloromethane, chloroform, carbon tetrachloride, ethers, such asdiethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethylether or ethylene glycol diethyl ether, nitriles, such as acetonitrileor propionitrile, amides, such as dimethylformamide, dimethylacetamide,N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorictriamide, or esters, such as ethyl acetate. The amines of the formula(XVII), in liquid form and in an appropriate excess, can also be used assolvents.

When carrying out the process (M-α) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between 0° C. and250° C., preferably at temperatures between 20° C. and 200° C.

The process (M-α) according to the invention is usually carried outunder atmospheric pressure. The process (M-α) according to the inventioncan be carried out under elevated pressure.

For carrying out the process (M-α) according to the invention, ingeneral from 1 to 20 mol, preferably from 1 to 5 mol, of amine of theformula (XVII) and, if appropriate, from 1 to 5 mol of dehydrating agentare employed per mole of the compounds of the formulae (I-1-a) to(I-4-a). The practice of the reaction and the work-up and isolation ofthe reaction products are carried out analogously to generally knownprocesses.

Suitable acids for the process (M-α) are organic acids, such as, forexample, acetic acid, trifluoroacetic acid or p-toluenesulphonic acid.

Suitable dehydrating agents for the process (M-α) are customary dryingagents, such as, for example, sodium sulphate, magnesium sulphate orcalcium chloride, and also molecular sieves. Moreover, the water ofreaction that is formed can be removed as an azeotrope by distillation.

The process (M-β) according to the invention for preparing the compoundsof the formulae (I-1-i) to (I-4-i) is characterized in that compounds ofthe formula (XVIII) are subjected to intramolecular condensation in thepresence of bases.

Diluents suitable for use in the process according to the invention forpreparing the compounds of the formulae (I-1-i) to (I-4-i) are allcustomary inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide, dimethylacetamide andN-methyl-pyrrolidone.

Deprotonating agents which can be used for carrying out the process(M-β) according to the invention for preparing the compounds of theformulae (I-1-i) to (I-4-i) are all customary proton acceptors.Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which can also be used in the presenceof phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutyl-ammonium chloride ortetrabutylammonium hydrogen sulphate, Adogen 464¹ or TDA 1². It isfurthermore possible to use alkali metal and alkaline earth metal amidesand hydrides, such as sodium amide, sodium hydride and calcium hydride,and furthermore also alkali metal alkoxides, such as sodium methoxide,sodium ethoxide and potassium tert-butoxide.

¹Adogen 464=methyltrialkyl(C₈-C₁₀)ammonium chloride

²TDA 1=tris-(methoxyethoxyethyl)-amine

When carrying out the process (M-β) according to the invention forpreparing the compounds of the formulae (I-1-i) to (I-4-i), the reactiontemperatures can be varied within a relatively wide range. In general,the process is carried out at temperatures between −20° C. and 250° C.,preferably between 0° C. and 150° C.

The process according to the invention is generally carried out underatmospheric pressure.

When carrying out the process (M-β) according to the invention forpreparing the compounds of the formulae (I-1-i) to (I-4-i), the reactioncomponents of the formula (XVIII) and the deprotonating bases aregenerally employed in approximately equimolar amounts. However, it isalso possible to employ a relatively large excess (up to 5 mol) of oneor the other component.

The process (N-α) is characterized in that compounds of the formulae(I-1-i¹) to (I-4-i¹) are reacted with acid halides of the formula (XIX).Diluents suitable for use in the process (N-α) according to theinvention when using the acid halides are all solvents which are inertto these compounds. Preference is given to using hydrocarbons, such asbenzine, benzene, toluene, xylene and tetraline, furthermore halogenatedhydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, nitrites, such asacetonitrile, and additionally solvents, such as dimethyl sulphoxide andsulpholane.

If acid binders are used in the reaction of the process (N-α) accordingto the invention, these can be all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,4-N,N-dimethylaminopyridine (DMAP), diazabicyclooctane (DABCO),diazabicycloundecene (DBU), diazabicyclononene (DBN), Hünig base andN,N-dimethyl-aniline, furthermore alkaline earth metal oxides, such asmagnesium oxide and calcium oxide, moreover alkali metal and alkalineearth metal carbonates, such as sodium carbonate, potassium carbonateand calcium carbonate, but also metal hydrides, such as sodium hydride.

In the process (N-α) according to the invention, even when using acidhalides, the reaction temperatures can be varied within a relativelywide range. In general, the process is carried out at temperaturesbetween −20° C. and +250° C., preferably between 0° C. and 150° C.

When carrying out the process (N-α) according to the invention, thestarting materials of the formulae (I-1-i¹) to (I-4-i¹) and the acidhalide of the formula (XIX) are generally employed in approximatelyequivalent amounts. However, it is also possible to employ a relativelylarge excess (up to 5 mol) of the acid chloride. Work-up is carried outby customary methods.

The process (N-β) is characterized in that compounds of the formulae(I-1-i¹) to (I-4-i¹) are reacted with carboxylic anhydrides of theformula (XX).

If, in the process (N-β) according to the invention, carboxylicanhydrides are used as reaction components of the formula (XX), thediluents used are preferably those diluents which are also preferablyused when employing acid halides. Otherwise, it is also possible forexcess carboxylic anhydride to act simultaneously as diluent. Preferredacid binders are the bases which are also preferably used when employingacid chlorides.

In the process (N-β) according to the invention, even when usingcarboxylic anhydrides, the reaction temperatures can be varied within arelatively wide range. In general, the processes are carried out attemperatures between −20° C. and +250° C., preferably between 0° C. and150° C.

When carrying out the process according to the invention, the startingmaterials of the formulae (I-1-i¹) to (I-4-i¹) and the carboxylicanhydride of the formula (XX) are generally employed in approximatelyequivalent amounts. However, it is also possible to employ a relativelylarge excess (up to 5 mol) of the carboxylic anhydride. Work-up iscarried out by customary methods.

In general, diluent and excess carboxylic anhydride and the carboxylicacid formed are removed by distillation or by washing with an organicsolvent or with water.

Furthermore, in the process (N), it is also possible to use mixtures ofacid chlorides of the formula (XIX) and carboxylic anhydrides of theformula (XX).

The process (N-γ) is characterized in that compounds of the formulae(1-1-a¹) to (I-4-a¹) are in each case reacted with orthoformic esters ofthe formula (XXI), in inert solvents. Preference is given to usinghydrocarbons, such as benzine, benzene, toluene, xylene and tetraline,furthermore halogenated hydrocarbons, such as methylene chloride,chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene,furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane,and also strongly polar solvents, such as dimethyl sulphoxide andsulpholane.

In the process (N-γ) according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the process is carried out at temperatures between −20° C. and +250° C.,preferably between 0° C. and 150° C.

When carrying out the process (N-γ) according to the invention, thestarting materials of the formulae (I-1-i¹) to (I-4-i¹) and theorthoformic ester of the formula (XXI) are generally each employed inapproximately equivalent amounts. However, it is also possible to usethe orthoformic ester in a relatively large excess (up to 5 mol) or evenas solvent. Work-up is carried out by customary methods.

The process (O) is characterized in that compounds of the formulae(I-1-i²) to (I-4-i²) are in each case reacted with carbonyl halides ofthe formula (XDI), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

Diluents suitable for use in the process (O) according to the inventionare all solvents which are inert to the acid halides. Preference isgiven to using hydrocarbons, such as benzine, benzene, toluene, xyleneand tetraline, furthermore halogenated hydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such as dimethylsulphoxide and sulpholane. The hydrolytic stability of the acid halidepermitting, the reaction can also be carried out in the presence ofwater.

Suitable acid binders for the reaction by the process (O) according tothe invention are all customary acid acceptors. Preference is given tousing tertiary amines, such as triethylamine, pyridine,N,N-dimethylaminopyridine (DMAP), diazabicyclooctane (DABCO),diazabicycloundecene (DBU), diazabicyclononene (DBN), Hünig base andN,N-dimethyl-aniline, furthermore alkaline earth metal oxides, such asmagnesium oxide and calcium oxide, moreover alkali metal and alkalineearth metal carbonates, such as sodium carbonate, potassium carbonateand calcium carbonate, and also alkali metal hydroxides, such as sodiumhydroxide and potassium hydroxide, but also metal hydrides, such assodium hydride.

In the process (O) according to the invention, the reaction temperaturescan be varied within a relatively wide range. In general, the process iscarried out at temperatures between −20° C. and +150° C., preferablybetween 0° C. and 100° C.

When carrying out the process (O) according to the invention, thestarting materials of the formulae (I-1-i²) to (I-4-i²) and the carbonylhalide of the formula (XIX) are generally each employed in approximatelyequivalent amounts. However, it is also possible to employ a relativelylarge excess (up to 5 mol) of the carbonyl halide. Work-up is carriedout by customary methods.

The active compounds are suitable for controlling animal pests, inparticular insects, arachnids and nematodes, which are encountered inagriculture, in forests, in the protection of stored products and ofmaterials, and in the hygiene sector, and have good plant tolerance andfavourable toxicity to warm-blooded animals. They may be preferablyemployed as crop protection agents. They are active against normallysensitive and resistant species and against all or some stages ofdevelopment. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanuscorporis, Haematopinus spp., Linognathus spp., Trichodectes spp. andDamalinia spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcomi, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp. and Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis, Costelytra zealandica and Lissorhoptrusoryzophilus.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Omithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., and Brevipalpus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp. and Bursaphelenchusspp.

If appropriate, the compounds according to the invention can, at certainconcentrations and application rates, also be employed as herbicides andmicrobicides, for example as fungicides, antimycotics and bactericides.If appropriate, they can also be used as intermediates or precursors inthe synthesis of other active compounds.

According to the invention, it is possible to treat all plants and partsof plants. Plants are to be understood here as meaning all plants andplant populations such as desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding plant cultivars which can or cannot be protected by plantbreeders certificates. Parts of plants are to be understood as meaningall above-ground and below-ground parts and organs of plants, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seedsand also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound and microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents, and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants, and/or foam-formers.

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol, and also their ethers and esters, ketones, such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, and also water.

As solid carriers there are suitable:

for example ammonium salts and ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as highly disperse silica,alumina and silicates; as solid carriers for granules there aresuitable: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, and also syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks;as emulsifiers and/or foam-formers there are suitable: for examplenonionic and anionic emulsifiers, such as polyoxyethylene fatty acidesters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand also protein hydrolysates; as dispersants there are suitable: forexample lignin-sulphite waste liquors and methylcellulose.

Tackifiers, such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants, such as inorganic pigments, for exampleiron.oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients, such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be present incommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, bactericides, acaricides,nematicides, fungicides, growth-regulating substances or herbicides. Theinsecticides include, for example, phosphoric acid esters, carbamates,carboxylates, chlorinated hydrocarbons, phenylureas and substancesproduced by microorganisms, inter alia.

Particularly favourable examples of co-components in mixtures are thefollowing compounds:

Fungicides:

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole,

flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium,fosetyl-sodium, fthatide, fuberidazole, furalaxyl, furametpyr,furcarbonil, furconazole, furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclasis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

(E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbarnate,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,

1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,

1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

2-phenylphenol (OPP),

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

8-hydroxyquinoline sulphate,

9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

potassium bicarbonate,

methanetetrathiol-sodium salt,

methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

N-((6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

N-formyl-N-hydroxy-DL-alanine-sodium salt,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/acaricides/nematicides:

abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avermectin, AZ60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopermethrin, BPMC, bromophosA, bufencarb, buprofezin, butathiofos, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cisperrnethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypennethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlorvos, diflubenzuron, dimethoate, dimethylvinphos,diofenolan, disulfoton, docusat-sodium, dofenapyn,

eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole,etrimfos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,farathiocarb,

granulosis viruses,

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

nuclear polyhedrosis viruses,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, monocrotophos,

naled, nitenpyram, nithiazine, novaluron,

omethoate, oxamyl, oxydemethon M,

Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur,prothiofos, prothoate, pymetrozine, pyraclofos, pyresmethrin, pyrethrum,pyridaben, pyridathion, pyrimidifen, pyriproxyfen,

quinalphos,

ribavirin,

salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate,triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron,trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii,

YI 5302,

zeta-cypermethrin, zolaprofos,

(1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,

2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

3-methylphenyl propylcarbamate,

4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

Bacillus thuringiensis strain EG-2348,

2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

It is also possible to admix other known active compounds, such asherbicides or fertilizers and growth regulators.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergistic agents are compoundswhich increase the action of the active compounds, without it beingnecessary for the synergistic agent added to be active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompounds are distinguished by an excellent residual action on wood andclay as well as a good stability to alkali on limed substrates.

The active compounds according to the invention act not only againstplant, hygiene and stored product pests, but also in the veterinarymedicine sector against animal parasites (ectoparasites), such as hardticks, soft ticks, mange mites, leaf mites, flies (biting and licking),parasitic fly larvae, lice, hair lice, feather lice and fleas. Theseparasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

From the subclass of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The active compound combinations of the formula (I) according to theinvention are also suitable for controlling arthropods which infestagricultural productive livestock, such as, for example, cattle, sheep,goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens,turkeys, ducks, geese and bees, other pets, such as, for example, dogs,cats, caged birds and aquarium fish, and also so-called test animals,such as, for example, hamsters, guinea pigs, rats and mice. Bycontrolling these arthropods, cases of death and reduction inproductivity (for meat, milk, wool, hides, eggs, honey etc.) should bediminished, so that more economic and easier animal husbandry ispossible by use of the active compounds according to the invention.

The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of moulded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

When used for cattle, poultry, pets and the like, the active compoundsof the formula (I) can be used as formulations (for example powders,emulsions, free-flowing compositions), which comprise the activecompounds in an amount of 1 to 80% by weight, directly or after 100 to10 000-fold dilution, or they can be used as a chemical bath.

It has furthermore been found that the active compounds according to theinvention also have a strong insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout a limitation:

Beetles, such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobiusmollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctusplanicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale,Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus,Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec.Dinoderus minutus.

Hymenopterons, such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites, such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,Coptotermes formosanus.

Bristletails, such as Lepisma saccarina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cards, leather, wood and processed wood products andcoating compositions.

Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

Wood and processed wood products which can be protected by the agentaccording to the invention or mixtures comprising this are to beunderstood as meaning, for example:

building timber, wooden beams, railway sleepers, bridge components, boatjetties, wooden vehicles, boxes, pallets, containers, telegraph poles,wood panelling, wooden windows and doors, plywood, chipboard, joinery orwooden products which are used quite generally in house-building or inbuilding joinery.

The active compounds can be used as such, in the form of concentrates orin generally customary formulations, such as powders, granules,solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersing agent and/or binder or fixing agent, awater repellent, if appropriate siccatives and UV stabilizers and, ifappropriate, dyestuffs and pigments, and also other processingauxiliaries.

The insecticidal compositions or concentrates used for the preservationof wood and wood-derived timber products comprise the active compoundaccording to the invention in a concentration of 0.0001 to 95% byweight, in particular 0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thenature and occurrence of the insects and on the medium. The optimumamount employed can be determined for the use in each case by a seriesof tests. In general, however, it is sufficient to employ 0.0001 to 20%by weight, preferably 0.001 to 10% by weight, of the active compound,based on the material to be preserved.

Solvents and/or diluents which are used are an organic chemical solventor solvent mixture and/or an oily or oil-like organic chemical solventor solvent mixture of low volatility and/or a polar organic chemicalsolvent or solvent mixture and/or water, and if appropriate anemulsifier and/or wetting agent.

Organic chemical solvents which are preferably used are oily or oil-likesolvents having an evaporation number above 35 and a flashpoint above30° C., preferably above 45° C. Substances which are used as such oilyor oil-like water-insoluble solvents of low volatility are appropriatemineral oils or aromatic fractions thereof, or solvent mixturescontaining mineral oils, preferably white spirit, petroleum and/oralkylbenzene.

Mineral oils having a boiling range from 170 to 220° C., white spirithaving a boiling range from 170 to 220° C., spindle oil having a boilingrange from 250 to 350° C., petroleum and aromatics having a boilingrange from 160 to 280° C., turpentine oil and the like, areadvantageously employed.

In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-like solvents of low volatility which have anevaporation number above 35 and a flashpoint above 30° C., preferablyabove 45° C., can be replaced in part by organic chemical solvents ofhigh or medium volatility, with the proviso that the solvent mixturelikewise has an evaporation number above 35 and a flashpoint above 30°C., preferably above 45° C., and that the insecticide/fungicide mixtureis soluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, some of the organic chemicalsolvent or solvent mixture is replaced by an aliphatic polar organicchemical solvent or solvent mixture. Aliphatic organic chemical solventscontaining hydroxyl and/or ester and/or ether groups, such as, forexample, glycol ethers, esters or the like, are preferably used.

Organic chemical binders which are used in the context of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se, are water-dilutable and/or are soluble or dispersible oremulsifiable in the organic chemical solvents employed, in particularbinders consisting of or comprising an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenolic resin, hydrocarbon resin, such as indene-cumarone resin,silicone resin, drying vegetable oils and/or drying oils and/orphysically drying binders based on a natural and/or synthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bituminous substances canalso be used as binders in an amount of up to 10% by weight. Dyestuffs,pigments, water-repelling agents, odour correctants and inhibitors oranticorrosive agents and the like which are known per se canadditionally be employed.

It is preferred according to the invention for the composition orconcentrate to comprise, as the organic chemical binder, at least onealkyd resin or modified alkyd resin and/or one drying vegetable oil.Alkyd resins having an oil content of more than 45% by weight,preferably 50 to 68% by weight, are preferably used according to theinvention.

All or some of the binder mentioned can be replaced by a fixing agent(mixture) or a plasticizer (mixture). These additives are intended toprevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

The plasticizers originate from the chemical classes of phthalic acidesters, such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoricacid esters, such as tributyl phosphate, adipic acid esters, such asdi-(2-ethylhexyl) adipate, stearates, such as butyl stearate or amylstearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

Fixing agents are based chemically on polyvinyl alkyl ethers, such as,for example, polyvinyl methyl ether or ketones, such as benzophenone orethylenebenzophenone.

Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementioned organicchemical solvents or diluents, emulsifiers and dispersing agents.

Particularly effective preservation of wood is achieved by impregnationprocesses on a large industrial scale, for example vacuum, double vacuumor pressure processes.

The ready-to-use compositions can also comprise other insecticides, ifappropriate, and also one or more fungicides, if appropriate.

Suitable additional mixing components are, preferably, the insecticidesand fungicides mentioned in WO 94/29 268. The compounds mentioned inthis document are an explicit constituent of the present application.

Especially preferred mixing components which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyphenoxideand triflumuron,

and also fungicides, such as epoxyconazole, hexaconazole, azaconazole,propiconazole, tebuconazole, cyproconazole, metconazole, imazalil,dichlorfluanid, tolylfluanid, 3-iodo-2-propinyl-butyl carbamate,N-octyl-isothiazolin-3-one and 4,5-di-chloro-N-octylisothiazolin-3-one.

The active compound combinations according to the invention can also beused for protecting against colonization of articles, especially ships'hulls, screens, nets, constructions, quays and signalling equipment,which come into contact with seawater or brackish water.

Colonization by sessile Oligochaetae, such as Serpulidae, and byshellfish and species of the group Ledamorpha (goose barnacles), such asvarious Lepas and Scalpellum species, or by species of the groupBalanomorpha (acorn barnacles), such as Balanus or Pollicipes species,increases the frictional resistance of ships and leads as a result,through increased energy consumption and frequent spells in dry dock, toa marked increase in the operating costs.

In addition to colonization by algae, for example Ectocarpus sp. andCeramium sp., particular importance is attached to infestation bysessile Entomostraca groups, which are comprised under the nameCirripedia (cirriped crustacea).

Surprisingly, it has now been found that the active compoundcombinations according to the invention, when used alone or incombination with other active compounds, have a good antifouling(anti-colonization) effect.

By using compounds according to the invention, either alone orcombination with other active compounds, it is possible to dispense withthe use of heavy metals, such as, for example, inbis(trialkyltin)sulphides, tri-n-butyltin laurate, tri-n-butyltinchloride, copper(I)oxide, triethyltin chloride,tri-n-butyl(2-phenyl-4-chlorophenoxy)-tin, tributyltin oxide, molybdenumdisulphide, antimony oxide, polymeric butyl titanate,phenyl-(bispyridine)-bismuth chloride, tri-n-butyltin fluoride,manganese ethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisthiocarbamate, the zinc and copper salts of 2-pyridinethiol1-oxide, bisdimethyldithiocarbamoylzinc ethylenebisthiocarbamate, zincoxide, copper(I)ethylene-bisdithiocarbamate, copper thiocyanate, coppernaphthenate and tributyltin halides, or substantially to reduce theconcentration of these compounds.

If appropriate, the ready-to-use antifouling paints may comprise yetfurther active compounds, preferably algicides, fungicides, herbicides,molluscicides or other antifouling active compounds.

Preferred co-components for the antifouling compositions according tothe invention are:

algicides, such as

2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,dichlorophen, diuron, endothal, fentin acetate, isoproturon,methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

fungicides, such as

cyclohexylbenzo[b]thiophenecarboxamide S,S-dioxide, dichlofluanid,fluor-folpet, 3-iodo-2-propinyl butylcarbamate, tolylfluanid and azoles,such as

azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole,propiconazole and tebuconazole;

molluscicides, such as

fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb andtrimethacarb;

or customary active antifouling active compounds, such as

4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethyl paratrylsulphone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium,copper, sodium and zinc salts of 2-pyridinethiole 1-oxide, pyridinetriphenylborane, tetrabutyldistannoxane,2,3,-5,6-tetrachloro-4-(methylsulphonyl)-pyridine,2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulphide and2,4,6-trichlorophenylmaleimide.

The antifouling compositions used comprise the active compound accordingto the invention in a concentration of from 0.001 to 50% by weight, inparticular from 0.01 to 20% by weight.

The antifouling compositions according to the invention furthermorecomprise the customary components as described, for example, in Ungerer,Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings,Noyes, Park Ridge, 1973.

In addition to the algicidal, fungicidal, molluscicidal and insecticidalactive compounds according to the invention, antifouling coatingcompositions comprise, in particular, binders.

Examples of acknowledged binders are polyvinyl chloride in a solventsystem, chlorinated rubber in a solvent system, acrylic resins in asolvent system especially in an aqueous system, vinyl chloride/vinylacetate copolymer systems in the form of aqueous dispersions or in theform of organic solvent systems, butadiene/styrene/acrylonitrilerubbers, drying oils, such as linseed oil, resin esters or modified hardresins in combination with tar or bitumen, asphalt and also epoxycompounds, small amounts of chlorinated rubber, chlorinatedpolypropylene and vinyl resins.

The coating compositions also optionally include inorganic pigments,organic pigments or dyestuffs, which are preferably insoluble in saltwater. The coating compositions may also comprise materials such asrosin, for a controlled release of the active compounds. The coats mayalso include plasticizers, modifying agents which influence therheological properties, and other conventional constituents. Thecompounds according to the invention or the abovementioned mixtures canalso be incorporated into self-polishing antifouling systems.

The active compounds are also suitable for controlling animal pests, inparticular insects, arachnids and mites, which are encountered in closedrooms, such as, for example, flats, factory halls, offices, vehiclecabins and the like. They can be used alone or in combination with otheractive compounds and auxiliaries in household insecticidal products forcontrolling these pests. They are active against sensitive and resistantspecies and against all stages of development. These pests include:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of the household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricacid esters, carbamates, pyrethroids, growth regulators or activecompounds from other known classes of insecticide.

They are used in the form of aerosols, unpressurized sprays, for examplepump and atomizer sprays, nebulizers, foggers, foams, gels, vaporizerproducts with vaporizer tablets made of cellulose or plastic, liquidvaporizers, gel and membrane vaporizers, propeller-operated vaporizers,energyless or passive vaporizer systems, moth papers, moth sachets andmoth gels, as granules or dusts, in baits for scattering or baitstations.

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.Weeds in the broadest sense is understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the zenera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, LQlium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The active compounds according to the invention are suitable, dependingon the concentration, for the total control of weeds, for example onindustrial terrain and rail tracks, and on paths and squares with andwithout tree plantings. Similarly, the active compounds according to theinvention can be employed for controllling weeds in perennial crops, forexample forests, decorative tree plantings, orchards, vineyards, citrusgroves, nut orchards, banana plantations, coffee plantations, teaplantations, rubber plantations, oil palm plantations, cocoaplantations, soft fruit plantings and hop fields, on lawns, turf andpastureland, and for the selective control of weeds in annual crops.

The compounds of the formula (I) according to the invention have strongherbicidal activity and a broad spectrum of activity when applied on thesoil and to above-ground parts of plants. To a certain extent, they arealso suitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothby the pre-emergence and by the post-emergence method.

At certain concentrations or application rates, the active compoundsaccording to the invention can also be employed for controlling animalpests and fungal or bacterial plant diseases. If appropriate, they canalso be used as intermediates or precursors for the synthesis of otheractive compounds.

According to the invention, it is possible to treat all plants and partsof plants. Plants are to be understood here as meaning all plants andplant populations such as desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding plant cultivars which can or cannot be protected by plantbreeders certificates. Parts of plants are to be understood as meaningall above-ground and below-ground parts and organs of plants, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seedsand also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspo-emulsion concentrates,natural and synthetic substances impregnated with active compound, andmicroencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is to say liquid solventsand/or solid carriers, optionally with the use of surfactants, that isto say emulsifiers and/or dispersants and/or foam-formers.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Liquid solvents which are mainlysuitable are: aromatics, such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols, such as butanol orglycol, and also their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethyl sulphoxide, andwater.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks, such as calcite, marble, pumice, sepiolite, dolomite andsynthetic granules of inorganic and organic meals, and granules oforganic material, such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers, such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use dyestuffs, such as inorganic pigments, for exampleiron oxide, titanium oxide, Prussian blue, and organic dyestuffs, suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients, such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in their formulations, can also be used as mixtures withknown herbicides and/or substances which improve the compatibility withcrop plants (“safeners”), finished formulations or tank mixes beingpossible. Also possible are mixtures with weed-killers comprising one ormore known herbicides and a safener.

Possible components for the mixtures are known herbicides, for example

acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, BAS-662H, beflubutamid,benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazon,benzfendizone, benzobicyclon, benzofenap, benzoylprop (-ethyl),bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim,bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl),chlomitrofen, chlorsulfuron, chlortoluron, cinidon (-ethyl),cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam (-methyl), cumyluron, cyanazine, cybutryne,cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D,2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P), diclofop(-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican,diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr,diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin,ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron,etobenzanid, fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl,-isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl),fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron,fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil,flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone,fluroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone,fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron, glufosinate(-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz (-methyl),imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr,imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin,isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole,isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet,mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron,metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metribuzin,metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide,neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl,oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat,pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham,picolinafen, piperophos, pretilachlor, primisulfuron (-methyl),profluazol, prometryn, propachlor, propanil, propaquizafop,propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfocarb,prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol,pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr,tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl),tritosulfuron.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied bothbefore and after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

The compounds according to the invention have a potent microbicidalactivity and can be employed for controlling undesirable microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides are employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides are employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above are mentioned as examples, but not by wayof limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Altemaria species, such as, for example, Altemaria brassicae; and

Pseudocercosporella species, such as, for example, Pseudocercosprellaherpotrichoides.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases pemits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

The active compounds according to the invention may also be employed toincrease the yield of crops. Moreover, they have reduced toxicity andare tolerated well by plants.

If appropriate, the active compounds according to the invention can, atcertain concentrations and application rates, also be employed asherbicides, for influencing plant growth and for controlling animalpests. If appropriate, they can also be used as intermediates andprecursors for the synthesis of other active compounds.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be adhesives, sizes, paper and board, textiles, leather,wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably adhesives, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds or compositions according tothe invention preferably act against fungi, in particular moulds,wood-discolouring and wood-destroying fungi (Basidiomycetes), andagainst slime organisms and algae.

Microorganisms of the following genera may be mentioned as examples:

Altemaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa, and

Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and micro-encapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Suitable liquidsolvents are essentially: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide or dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as highlydisperse silica, alumina and silicates. Suitable solid carriers forgranules are: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, or else syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks.Suitable emulsifiers and/or foam formers are: for example nonionic andanionic emulsifiers, such as polyoxyethylene fatty acid esters,polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or elseprotein hydrolysates. Suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such orin their formulations also mixed with known fungicides, bactericides,acaricides, nematicides or insecticides in order thus, for example, towiden the spectrum of action or to prevent development of resistance. Inmany cases, synergistic effects are achieved, i.e. the activity of themixture exceeds the activity of the individual components.

Examples of co-components in mixtures are the following compounds:

Fungicides:

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, iso-prothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclasis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

(E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone-O-(phenylmethyl)-oxime,

1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,

1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

2-[(1-methylethyl)sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-clucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

2-phenylphenol (OPP),

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

3,5-dichloro-N-[cyano-[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

8-hydroxyquinoline sulphate,

9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)oxy]-2,5-thiophenedicarboxylate,

cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethylmorpholinehydrochloride,

ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

potassium hydrogen carbonate,

methanetetrathiol sodium salt,

methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

N-formyl-N-hydroxy-DL-alanine sodium salt,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

spiro[2H]-1-benzopyran-2,1′(3′H)-isobenzofuran]-3′-one,

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/acaricides/nematicides:

abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,aldoxycarb, alpha-cypernethrin, alphamethrin, amitraz, avermectin, AZ60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopernethrin, BPMC, bromophosA, bufencarb, buprofezin, butathiofos, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlorvos, diflubenzuron, dimethoate, dimethylvinphos,diofenolan, disulfoton, docusat-sodium, dofenapyn,

eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole,etrimfos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,furathiocarb,

granulosis viruses,

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

nuclear polyhedrosis viruses,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, monocrotophos,

naled, nitenpyram, nithiazine, novaluron,

omethoate, oxamyl, oxydemethon M,

Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur,prothiofos, prothoate, pymetrozine, pyraclofos, pyresmethrin, pyrethrum,pyridaben, pyridathion, pyrimidifen, pyriproxyfen,

quinalphos,

ribavirin,

salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate,triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron,trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii,

YI 5302,

zeta-cypermethrin, zolaprofos,

(1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,

2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

3-methylphenyl propylcarbamate,

4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

Bacillus thuringiensis strain EG-2348,

[2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

It is also possible to admix other known active compounds, such asherbicides or fertilizers and growth regulators.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, moulds and diphasic fungi (for example against Candida speciessuch as Candida albicans, Candida glabrata), Epidermophyton species,such as Epidermophyton floccosum, Aspergillus species such asAspergillus niger and Aspergillus fumigatus, Trichophyton species suchas Trichophyton mentagrophytes, Microsporon species such as Microsporoncanis and audouinii. The list of these fungi does by no means limit themycotic spectrum covered, but is only for illustration.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. They are used in the customary manner, for example bypouring, spraying, atomizing, spreading, foaming, brushing on and thelike. It is further possible to apply the active compounds by theultra-low volume method or to inject the active compound formulation, orthe active compound itself, into the soil. The seed of the plants canalso be treated.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the type of application. In the treatment of partsof plants, the application rates of active compound are generallybetween 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. In thetreatment of seed, the application rates of active compound aregenerally between 0.001 and 50 g per kilogram of seed, preferablybetween 0.01 and 10 g per kilogram of seed. In the treatment of thesoil, the application rates of active compound are generally between 0.1and 10,000 g/ha, preferably between 1 and 5000 g/ha.

The preparation and the use of the substances according to the inventionis illustrated by the examples below.

PREPARATION EXAMPLES Example I-1-a-1

At rom 20° C. to 40° C., 0.5 g of the compound according to ExampleII-1, dissolved in 1 ml of anhydrous dimethylformamide (DMF), is addeddropwise to 0.4 g of potassium tert-butoxide in 1 ml of anhydrous DMF,the mixture is stirred at 40° C. and the reaction is monitored bythin-layer chromatography. After the reaction has ended, 10 ml ofice-water are added to the reaction mixture, which is, at from 0° C. to10° C., acidified to pH 2 using conc. hydrochloric acid and thenfiltered off with suction. The residue is washed with ice-water andpurified by silica gel chromatography using methylene chloride/ethylacetate 3:1 as mobile phase.

Yield: 0.3 g ( 64% of theory), m.p. 168° C.

The following compounds of the formula (I-1-a) were prepared analogouslyto Example I-1-a-1 and/or according to the general statements about thepreparation of compounds of the formula (I-1-a).

TABLE 1 (I-1-a)

m.p. Ex. No. V W X Y Z B A D m ° C. isomer I-1-a-2 H Cl Cl H H CH₃ CH₃ H2 112-114 — I-1-a-3 F H F F F CH₃ CH₃ H 2 112 — I-1-a-4 H H Cl Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— H 2 199 β I-1-a-5 H H Cl Cl H—(CH₂)₂—CHCH₃—(CH₂)₂— H 2 208 β I-1-a-6 H Cl Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— H 2 230 β I-1-a-7 H Cl Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— H 2 130 β I-1-a-8 Cl H H CF₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— H 2 149 β I-1-a-9 H H Cl Cl H—(CH₂)₂—CHOC₂H₅—(CH₂)₂— H 2 173 β I-1-a-10 H Cl Cl H H—(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 2 250 β I-1-a-11 H H H Cl H H

H 2 182 — I-1-a-12 H H NO₂ H H H

H 2 MS/ESI M 345 (100%) — I-1-a-13 H H H Cl H H

H 2 169-170 — I-1-a-14 H H NO₂ H H H

H 2 MS-ESI M 379 (100%) — I-1-a-15 H H Cl Cl H —(CH₂)₂—O—(CH₂)₂— H 2 220— I-1-a-16 H H Cl Cl H —CH₂—O—(CH₂)₃ H 2 189 —

Example I-1-b-1

0.23 g (0.59 mmol) of the compound according to Example I-1-a-9 isinitially charged in 2 ml of absolute methylene chloride, 0.06 g (0.59mmol) of triethylamine is added and 0.065 g (0.59 mmol) of isobutyrylchloride in 1 ml of absolute methylene chloride is added dropwise. Themixture is stirred under reflux overnight and washed with water, theaqueous phase is extracted with methylene chloride and the combinedmethylene chloride phases are dried over MgSO₄ and concentrated, and thecrystalline residue is stirred with cleaner's naphtha. The solid isfiltered off with suction and dried in air.

Yield: 0.135 g (49.5% oftheory), m.p.: 112° C.

The following compounds of the formulae (I-1-b) and (I-1-c) wereprepared analogously to Example I-1-b-1:

TABLE 1′ m.p. Ex. No. V W X Y Z R¹ R² D L M A B ° C. I-1-b-1 H H Cl Cl HCH—(CH₃)₂ — H — —

112° C. I-1-b-2 H H Cl Cl H CH—(CH₃)₂ — H — — —CH₂—O—(CH₂)₃ 120° C.I-1-b-3 H H Cl Cl H CH—(CH₃)₂ — H — — —(CH₂)₂—O—(CH₂)₂— 145° C. I-1-c-1H H Cl Cl H — CH₂—CH—(CH₃)₂ H O O

124° C. I-1-c-2 H H Cl Cl H — CH₂—CH—(CH₃)₂ H O O —CH₂—O—(CH₂)₃ 121° C.I-1-c-3 H H Cl Cl H — C₂H₅ H O O —(CH₂)₂—O—(CH₂)₂— 162° C. I-1-c-4 H HCl Cl H — CH₂—CH—(CH₃)₂ H O O —(CH₂)₂—O—(CH₂)₂— 154° C.

Example I-1-i-1

At 40° C., 5.5 g of the compound according to Example XVIII-1, suspendedin 5 ml of anhydrous DMF, are added dropwise to 5 g of potassiumtert-butoxide in 30 ml of anhydrous DMF, and the mixture is stirred at60° C. for 2 hours. The solvent is distilled off under reduced pressureand the residue is taken up in water, stirred into 200 ml of 20%strength hydrochloric acid, filtered off with suction and dried. Theresidue is purified by silica gel chromatography using methylenechloride/ethyl acetate 5:3 as mobile phase.

Yield: 2.3 g ( 42% of theory), m.p. 175° C.

Example I-1-i-2

0.51 g of the compound (I-1-i-1), 0.15 g of acetyl chloride and 0.2 g ofacetic anhydride in 20 ml of anhydrous toluene are heated at 60° C., andthe progress of the reaction is monitored by thin-layer chromatography.The solvent is distilled off under reduced pressure and the residue ispurified by silica gel chromatography using methylene chloride/ethylacetate 5:3 as mobile phase.

Yield: 0.35 g ( 61% of theory), m.p. 196° C.

Example I-1-i-3

At 0° C., 0.35 g of the compound (I-1-i-1) in 30 ml of anhydroustetrahydrofuran (THF) is added dropwise to 0.04 g of sodium hydride(60%) in 10 ml of anhydrous THF. At 20° C., 0.1 g of acetyl chloride isthen added dropwise, and the mixture is then stirred at 20° C., theprogress of the reaction being monitored by thin-layer chromatography.The mixture is carefully admixed with water and extracted with methylenechloride, and the extract is dried and concentrated. The residue ispurified by silica gel chromatography using methylene chloride/ethylacetate 3:1 as mobile phase.

Yield: 0.35 g ( 99% of theory), m.p. 142° C.

Example I-1-i-4

1.4 g of the compound (XVIII-1′-9) are initially charged in 100 ml ofacetonitrile. After addition of 0.93 g of benzyl bromide and 1.02 g ofpotassium carbonate, the mixture is heated under reflux for 22 hours.The precipitate is filtered off with suction, the filtrate isconcentrated and the residue is stirred with ether/acetone, filtered offwith suction and dried.

Yield: 1.1 g ( 59% of theory), m.p. 190° C.

The following compounds of the formula (I-1-i) were prepared analogouslyto Examples (I-1-i-1) to (I-1-i-4) and/or in accordance with the generalstatements on the preparation of compounds of the formula (I-1-i):

TABLE 2 (I-1-i)

m.p. Ex. No. V W X Y Z B A D m R⁹ R¹⁰ ° C. I-1-i-5 CF₃ H H Cl H CH₃ CH₃H 2 H H 173 I-1-i-6 H Cl Cl CF₃ H CH₃ CH₃ H 2 H H I-1-i-7 H H Cl Cl HCH₃ CH₃ H 2 H H 228 I-1-i-8 H H Cl Cl H CH₃ CH₃ H 2 H CO—CH₃ 230 I-1-i-9H H Cl Cl H CH₃ CH₃ CH₃CO— 2 H H >250   I-1-i-10 H H H OCF₃ H CH₃ CH₃

2 H H 182 I-1-i-11 H H H OCF₃ H CH₃ CH₃

2 H H 195 I-1-i-12 NO₂ H H H H CH₃ CH₃

2 H H 180 I-1-i-13 H H H F H CH₃ CH₃

2 H H 162

Example II-1

3.04 g of methyl aminoisobutyrate hydrochloride are initially charged in50 ml of anhydrous tetrahydrofuran (THF). After addition of 5.6 ml oftriethylamine, 2.6 g of 2,4-dichlorobenzylsulphonyl chloride, dissolvedin 10 ml of anhydrous THF, are added dropwise, and the mixture isstirred at room temperature for 1 h. The reaction mixture is poured into200 ml of 1 N hydrochloric acid and extracted with methylene chloride,the extract is dried and the solvent is distilled off. The residue ispurified by silica gel chromatography using ethyl acetate/n-hexane 2:1as mobile phase.

Yield 0.68 g (24% of theory), m.p.: 84° C.

Example II-2

At room temperature, 0.04 g (0.94 mmol) of sodium hydride (60%) isinitially charged in 2 ml of absolute dimethylformamide, and 0.37 g(0.94 mmol) of methyl1-[[[(2,6-dichlorophenyl)methyl]sulphonyl]-amino]-4-methylcyclohexane-carboxylate,dissolved in 1 ml of absolute dimethylformamide, is added. The mixtureis stirred at room temperature for 10 minutes, 0.2 g (1.41 mmol) ofmethyl iodide is then added dropwise, and the mixture is stirred at roomtemperature overnight. The mixture is poured into ice-water and madeslightly acidic using concentrated hydrochloric acid, and the solid isfiltered off with suction and dried in the air.

Yield: 0.325 g (84.8% of theory); Melting point: 100° C.

The following compounds of the formula (II) were prepared analogously toExamples II-1 and II-2 and/or in accordance with the general statementson the preparation of compounds of the formula (II):

TABLE 3 (II)

m.p. Ex. No. V W X Y Z B A D m R¹² ° C. isomer II-3 H Cl Cl H H CH₃ CH₃H 2 CH₃ 115 — II-4 H H F H H CH₃ CH₃ H 2 CH₃  67 — II-5 H H CF₃ H H CH₃CH₃ H 2 CH₃ — II-6 H H H F H CH₃ CH₃ H 2 CH₃  53 — II-7 F H H H H CH₃CH₃ H 2 CH₃  56 — II-8 CF₃ H H Cl H CH₃ CH₃ H 2 CH₃  85 — II-9 F F F F HCH₃ CH₃ H 2 CH₃  91 — II-10 H H Cl Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— H 2 CH₃102 β II-11 H H Cl Cl H —(CH₂)₂—CHCH₃—(CH₂)₂— H 2 CH₃ 103 β II-12 H ClCl H H —(CH₂)₂—CHOCH₃—(CH₂)₂— H 2 CH₃ 103 β II-13 H H Cl Cl H—(CH₂)₂—CHOC₂H₅—(CH₂)₂— H 2 CH₃ 133 β II-14 H H Cl Cl H—(CH₂)₂—CHCH₃—(CH₂)₂— H 2 CH₃ 195 β II-15 Cl H H CF₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— H 2 CH₃ oil β II-16 H H Cl Cl H—(CH₂)₂—CHOC₂H₅—(CH₂)₂— H 2 CH₃ 129 β II-17 H H NO₂ H H H

H 2 CH₃ MS-FAB M⁺ 411 (100%) — II-18 H H H Cl H H

H 2 CH₃ 106 — II-19 H H NO₂ H H H

H 2 CH₃  91 — II-20 H H H Cl H H

H 2 CH₃ 144--46 — II-21 H H Cl Cl H —(CH₂)₂—O—(CH₂)₂— H 2 CH₃ 130 —II-22 H H Cl Cl H —CH₂—O(CH₂)₃— H 2 CH₃  93 —

Ex. No. V W X Y Z B A D m R¹² m.p. ° C. II-23 H H Br Br F—(CH₂)—O—(CH)₃— H 2 CH₃ 129° C. II-24 H H Br Br F —(CH₂)₂—CHOCH₃—(CH₂)₂—H 2 CH₃ 105° C. II-25 Cl H H H Cl —(CH₂)₂—CHOCH₃—(CH₂)₂— H 2 CH₃  65° C.II-26 Cl H H H Cl —(CH₂)—O—(CH₂)₃— H 2 CH₃ 148° C. II-27 Cl H H H Cl—(CH₂)₂—O—(CH₂)₂— H 2 CH₃ 210° C. II-28 H H Br Br F —(CH₂)₂—O—(CH₂)₂— H2 CH₃ 150° C.

Example XVIII-II′-1

1.7 g of 2-amino-isobutyronitrile are initially charged in 40 ml ofanhydrous tetrahydrofuran (THF). 2.8 ml of triethylamine are added, and5 g of 3-trifluoromethyl-benzylsulfonyl chloride, dissolved in 10 ml ofanhydrous THF, are then added dropwise at 0° C. The mixture is stirredat 20° C. for 1 hour, then stirred into 200 ml of 1 N hydrochloric acidand extracted, the extract is dried and the solvent is evaporated underreduced pressure. The residue is purified by silica gel chromatographyusing hexane/ethyl acetate 7:3 as mobile phase.

Yield: 6.1 g (=99% of theory), m.p.: 107° C.

The following compounds are prepared analogously to Example (XVIII-1′-1)and/or in accordance with the general statements on the preparation ofcompounds of the formula (XVIII-1′):

TABLE 4 (XVIII-1′)

m.p. Ex. No. V W X Y Z B A D m ° C. XVIII-1′-2 H H Cl Cl H CH₃ CH₃ H 2138 XVIII-1′-3 H Cl Cl CF₃ H CH₃ CH₃ H 2 128 XVIII-1′-4 H H CF₃ H H CH₃CH₃ H 2 XVIII-1′-5 CF₃ H H Cl H CH₃ CH₃ H 2 XVIII-1′-6 H H Cl Cl H—(CH₂)₅— H 2 XVIII-1′-7 H Cl Cl H H —(CH₂)₅— H 2 188 XVIII-1′-8 H H HOCF₃ H CH₃ CH₃ H 2 126 XVIII-1′-9 NO₂ H H H H CH₃ CH₃ H 2 135XVIII-1′-10 H H H F H CH₃ CH₃ H 2 oil

Example I-2-a-1

0.73 g (18.2 mmol) of sodium hydride (60%) are initially charged in 4 mlof absolute dimethylformamide, the mixture is cooled to 0° C. and 3.1 g(9.1 mmol) of methyl2-{[(2,4-dichlorobenzyl)sulphonyl]oxy}-2-methylpropanoate according toExample (III-1) in 5 ml of absolute dimethylformamide are addeddropwise. The mixture is stirred at room temperature overnight and thenpoured onto ice, acidified using concentrated hydrochloric acid andextracted repeatedly with methylene chloride. The extract is dried overmagnesium sulphate and concentrated, giving the compound I-2-a-1 as ayellow oil.

Yield: 2 g (71% of theory); ¹H-NMR (400 MHz, CDCl₃): δ=1.65, s, 6H(2×CH₃); 7.49, dd, 1H; 7.55, dd, 1H; 7.8 1, d, 1H; 12.6, bs, 1H;

The following compounds of the formula (I-2-a) were prepared analogouslyto Example I-2-a-1 and/or in accordance with the general statements onthe preparation of compounds of the formula (I-2-a):

TABLE 5 (I-2-a)

m.p. Ex. No. V W X Y Z A B m ° C. I-2-a-2 H H H CF₃ H CH₃ CH₃ 2  90I-2-a-3 NO₂ H H H H CH₃ CH₃ 2  83 I-2-a-4 H H F CF₃ H CH₃ CH₃ 2  70I-2-a-5 F F F F H CH₃ CH₃ 2 oil I-2-a-6 CF₃ H H Cl H CH₃ CH₃ 2 oilI-2-a-7 H Cl Cl H H CH₃ CH₃ 2 200 I-2-a-8 H H Cl Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— 2 oil I-2-a-9 H H Cl Cl H —(CH₂)₂—CHCH₃—(CH₂)₂— 2oil I-2-a-10 H H Cl Cl H —(CH₂)₂—CHOC₂H₅—(CH₂)₂— 2 oil I-2-a-11 H Cl ClH H —(CH₂)₂—CHCH₃—(CH₂)₂— 2 oil I-2-a-12 H Cl Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— 2 248

Example I-2-i-1

4 g of the compound XVIII-2′-1 are initially charged in 25 ml ofacetonitrile. After addition of 0.24 g of diazabicycloundecene (DBU),the mixture warms to 32° C. Stirring at room temperature is continuedfor a further 7 h, and the mixture is then concentrated. The residue issuspended in toluene/diisopropyl ether, filtered off with suction anddried.

Yield: 3.6 g ( 90% of theory), m.p. 201° C.

The following compounds of the formula (I-2-i) were prepared analogouslyto Example I-2-i-1 and/or in accordance with the general statements onthe preparation of compounds of the formula (I-2-i):

TABLE 6 (I-2-i)

m.p. Ex. No. V W X Y Z A B R⁹ R¹⁰ ° C. I-2-i-2 CF₃ H H H H CH₃ CH₃ H H181 I-2-i-3 H H H OCF₃ H CH₃ CH₃ H H 126 I-2-i-4 NO₂ H H H H CH₃ CH₃ H H186 where m = 2

Example III-1

At 0° C., 1.24 g (10.5 mmol) of methyl 2-hydroxyisobutyrate areinitially charged in 11 ml of pyridine, and 3 g (11.5 mmol) of2,4-dichlorobenzylsulphonyl chloride are added a little at a time. Themixture is allowed to stand in a fridge at 5° C. for 5 days and thenpoured onto 50 g of ice, 10.5 g of concentrated sulfuric acid are added,the mixture is extracted with methyl tert-butyl ether, and the extractis dried over magnesium sulphate and concentrated, giving the compoundIII-1 as an oil.

Yield: 3.22 g (81.6% of theory); ¹H-NMR (400 MHz, CDCl₃): δ=1.7, s, 6H(2×CH₃); 3.75, s, 3H (OCH₃); 4.67, s, 2H (CH₂); 7.28, dd, 1H; 7.5, m,2H.

The following compounds of the formula (III) were prepared analogouslyto Example III-1 and/or in accordance with the general statements on thepreparation of the compounds of the formula (III).

TABLE 7 (III)

m.p. Ex. No. V W X Y Z A B m R¹² ° C. III-2 H H H CF₃ H CH₃ CH₃ 2 CH₃oil III-3 NO₂ H H H H CH₃ CH₃ 2 CH₃ oil III-4 H H F CF₃ H CH₃ CH₃ 2 CH₃oil III-5 F F F F H CH₃ CH₃ 2 CH₃ oil III-6 CF₃ H H Cl H CH₃ CH₃ 2 CH₃oil III-7 H Cl Cl H H CH₃ CH₃ 2 CH₃   97.5 III-8 H H Cl Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂ 2 C₂H₅ oil III-9 H H Cl Cl H —(CH₂)₂—CHCH₃—(CH₂)₂2 C₂H₅ oil III-10 H H Cl Cl H —(CH₂)₂—CHOC₂H₅—(CH₂)₂ 2 C₂H₅ oil III-11 HCl Cl H H —(CH₂)₂—CHCH₃—(CH₂)₂ 2 C₂H₅ oil III-12 H Cl Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂ 2 C₂H₅ 99

Example XVIII-2′-1

4.48 g of 2-hydroxyisobutyronitrile are initially charged in 120 ml ofmethylene chloride and admixed with 7.2 g of triethylamine, 10 g of4-fluorobenzyl-sulphonyl chloride are added dropwise at 0° C. and themixture is stirred at room temperature for 6 h. The reaction solution istaken up in water and the organic phase is separated off, dried andconcentrated. The residue is purified by silica gel chromatography usingtoluene/ether 10:1 as mobile phase.

Yield: 5.1 g ( 37% of theory), m.p. 68° C.

The following compounds of the formula (XVIII-2′) were preparedanalogously to Example XVIII-2′-1 and/or in accordance with the generalstatements on the preparation of compounds of the formula (XVIII-2′).

TABLE 8 (XVIII-2′)

m.p. Ex. No. V W X Y Z A B ° C. XVIII-2′-2 CF₃ H H H H CH₃ CH₃ 63XVIII-2′-3 H H H OCF₃ H CH₃ CH₃ 68 XVIII-2′-4 NO₂ H H H H CH₃ CH₃ 85where m = 2

Example I-3-a-1

0.81 g (20.2 mmol) of sodium hydride (60%) is initially charged in 5 mlof absolute dimethylformamide, and 3.2 g (9.63 mmol) of methyl2-[[(2,4,6-trimethylphenyl)-methyl]sulphonyl]-benzoate in 5 ml ofabsolute dimethylformamide are added dropwise. The mixture is stirred atroom temperature overnight, poured into ice-water and acidified withhydrochloric acid, and the solid is filtered off with suction, washedwith ice-water and cleaner's naphtha and dried in the air.

Yield: 3 g (quantitative); Melting point: 220-225° C.

The following compounds of the formula I-3-a were prepared analogouslyto Example I-3-a-1 and/or in accordance with the general statements onthe preparation of compounds of the formula (I-3-a):

TABLE 9 I-3-a

m.p. Ex. No. V W X Y Z A Q¹ m ° C. I-3-a-2 H H Cl —O—CH₂—O——CH═CH—CH═CH— 2 210-214 I-3-a-3 H H Cl Cl H —CH═CH—CH═CH— 2 152-157I-3-a-4 H H Cl CHF₂ Cl —CH═CH—CH═CH— 2 177-182 I-3-a-5 H H CH₃ CH₃ CH₃—CH═CH—CH═CH— 2 179-182 I-3-a-6 H H F CF₃ H —CH═CH—CH═CH— 2 109-112I-3-a-7 CH₃ CH₃ CH₃ CH₃ H —CH═CH—CH═CH— 2 143-145 I-3-a-8 H H CH₃ CH₃ H—CH═CH—CH═CH— 2 188 I-3-a-9 H H Br CH₃ Br —CH═CH—CH═CH— 2 204-208I-3-a-10 Br CH₃ CH₃ CH₃ H —CH═CH—CH═CH— 2 160-163 I-3-a-11 H H Cl Cl Cl—CH═CH—CH═CH— 2 178 I-3-a-15 H H CH₃ H CH₃ —CH═CH—CH═CH— 2 178 I-3-a-16H H CH₃ OCH₃ CH₃ —CH═CH—CH═CH— 2 177 I-3-a-17 Phenyl H CH₃ H H—CH═CH—CH═CH— 2 204 I-3-a-19 H H OCH₃ Cl Br —CH═CH—CH═CH— 2  98 I-3-a-20H H CF₃ Cl H —CH═CH—CH═CH— 2 184 I-3-a-21 H H CF₃ CF₃ H —CH═CH—CH═CH— 2141 I-3-a-22 Cl H F F Cl —CH═CH—CH═CH— 2 I-3-a-23 H CH₃ CH₃ CH₃ H—(CH₂)₃ 2 172 I-3-a-24 H Cl Cl H H —(CH₂)₃ 2 179 I-3-a-25 Cl Cl H H H—(CH₂)₃ 2 157 I-3-a-26 H H Cl Cl H —(CH₂)₃ 2 180 I-3-a-27 H H OCH₃ CH₃Cl —(CH₂)₃ 2 116 I-3-a-29 H CH₃ CH₃ CH₃ H —(CH₂)₂—C(CH₃)₂—CH₂— 2 157

Example I-3-i-1

0.52 g of sodium hydride (60%) is initially charged in 8 ml of anhydrousdimethylformamide, and with ice-cooling, 4.2 g of the compound accordingto Example XVIII-3′-1, dissolved in 8 ml of anhydrous dimethylformamide,are added dropwise. The mixture is stirred at room temperatureovernight, poured into ice-water and neutralized with hydrochloric acid,and the solid is filtered off with suction and dried.

Yield: 4.2 g ( 100% of theory), m.p. 242-245° C.

Example I-3-i-2 of melting point 268-270° C. is obtained analogously toExample 1-3-i-1.

Example IV-1

2.9 g (9.65 mmol) of methyl2-[[(2,4,6-trimethylphenyl)methyl]thio]-benzoate are initially chargedin 30 ml of CH₂Cl₂, and 6.66 g (19.3 mmol) of m-chloroperbenzoic acid(50% strength) are added a little at a time. The mixture is stirred atroom temperature overnight and filtered off with suction, and thefiltrate is admixed with 0.5 ml of dimethyl sulphide and stirred at roomtemperature for 1 hour. The filtrate is admixed with 50 ml of saturatedNaHCO₃ solution and stirred at room temperature for 30 minutes. Theaqueous phase is separated off and extracted twice with CH₂Cl₂, and thecombined organic phases are dried and concentrated.

Yield: 3.3 g (quantitative), melting point: 132-136° C.

The following compounds of the formula (IV) are obtained analogously toExample IV-1 and/or in accordance with the general statements of thepreparation of compounds of the formula (IV):

TABLE 10 (IV)

Ex. No. V W X Y Z A Q¹ m R¹² m.p. ° C. IV-2 H H Cl —CH₂—O—CH₂——CH═CH—CH═CH— 2 CH₃ 148-154 IV-3 H H Cl Cl H —CH═CH—CH═CH— 2 CH₃ 69-71IV-4 H H Cl CHF₂ Cl —CH═CH—CH═CH— 2 CH₃ 114-119 IV-5 H H CH₃ CH₃ CH₃—CH═CH—CH═CH— 2 CH₃ oil IV-6 H H F CF₃ H —CH═CH—CH═CH— 2 CH₃  99-103IV-7 CH₃ CH₃ CH₃ CH₃ H —CH═CH—CH═CH— 2 CH₃ oil IV-8 H H CH₃ CH₃ H—CH═CH—CH═CH— 2 CH₃ oil IV-9 H H Br CH₃ Br —CH═CH—CH═CH— 2 CH₃ 160-163IV-10 Br CH₃ CH₃ CH₃ H —CH═CH—CH═CH— 2 CH₃ 137-138 IV-11 H H Cl Cl Cl—CH═CH—CH═CH— 2 CH₃ 160-165 IV-15 H H CH₃ H CH₃ —CH═CH—CH═CH— 2 CH₃164-168 IV-16 H H CH₃ OCH₃ CH₃ —CH═CH—CH═CH— 2 CH₃ 154-157 IV-17 phenylH CH₃ H H —CH═CH—CH═CH— 2 CH₃ 113-115 IV-19 H H F Cl Br —CH═CH—CH═CH— 2CH₃ 136-139 IV-20 H H CF₃ Cl H —CH═CH—CH═CH— 2 CH₃ 119-123 IV-21 H H CF₃CF₃ H —CH═CH—CH═CH— 2 CH₃  94 IV-22 Cl H F F Cl —CH═CH—CH═CH— 2 CH₃168-170 IV-23 H CH₃ CH₃ CH₃ H —(CH₂)₃— 2 CH₃ 145 IV-24 H Cl Cl H H—(CH₂)₃— 2 CH₃ oil IV-25 Cl Cl H H H —(CH₂)₃— 2 CH₃ oil IV-26 H H Cl ClH —(CH₂)₃— 2 CH₃ oil IV-27 H H OCH₃ CH₃ Cl —(CH₂)₃— 2 CH₃ oil IV-29 HCH₃ CH₃ CH₃ H —(CH₂)₂—C(CH₃)₂—CH₂— 2 CH₃ 165

Example XXXI-1

0.864 g (16 mmol) of sodium methoxide is dissolved in 15 ml of absolutemethanol, 2.52 g (15 mmol) of methyl thiosalicylate are added and 2.53 g(15 mmol) of 2,4,6-trimethylbenzyl chloride are then slowly addeddropwise. The mixture is stirred at room temperature overnight,concentrated and admixed with water, and the crystals are filtered offwith suction, washed with cleaner's naphtha and dried in the air.

Yield: 2.98 g (66.1% of theory), melting point: 115-118° C.

The following compounds of the formula (XXXI) were prepared analogouslyto Example XXXI-1 and/or in. accordance with the general statements onthe preparation of compounds of the formula (XXXI):

TABLE 11 (XXXI)

Ex. No. V W X Y Z A Q¹ R¹² m.p. ° C. XXXI-2 H H Cl —O—CH₂—O——CH═CH—CH═CH— CH₃ 120-123 XXXI-3 H H Cl Cl H —CH═CH—CH═CH— CH₃ 111-115XXXI-4 H H Cl CHF₂ Cl —CH═CH—CH═CH— CH₃ 126-129 XXXI-5 H H CH₃ CH₃ CH₃—CH═CH—CH═CH— CH₃ 104-106 XXXI-6 H H F CF₃ H —CH═CH—CH═CH— CH₃ 112-115XXXI-7 CH₃ CH₃ CH₃ CH₃ H —CH═CH—CH═CH— CH₃ 131-134 XXXI-8 H H CH₃ CH₃ H—CH═CH—CH═CH— CH₃  79 XXXI-9 H H Br CH₃ Br —CH═CH—CH═CH— CH₃ 143 XXXI-10Br CH₃ CH₃ CH₃ H —CH═CH—CH═CH— CH₃ 125 XXXI-11 H H F Cl Br —CH═CH—CH═CH—CH₃ 106 XXXI-12 H H CF₃ Cl H —CH═CH—CH═CH— CH₃ 82-83 XXXI-13 H H CF₃ CF₃H —CH═CH—CH═CH— CH₃ 108-111 XXXI-14 Cl H F F Cl —CH═CH—CH═CH— CH₃132-135 XXXI-15 H H Cl Cl Cl —CH═CH—CH═CH— CH₃ 148 XXXI-19 H H CH₃ H CH₃—CH═CH—CH═CH— CH₃ 135-139 XXXI-20 H H CH₃ OCH₃ CH₃ —CH═CH—CH═CH— CH₃143-146 XXXI-21 phenyl H CH₃ H H —CH═CH—CH═CH— CH₃  91

Example XVIII-3′-1

4.7 g of the compound according to Example XXXVI-1 are initially chargedin 90 ml of methylene chloride and, at room temperature, 11.03 g ofm-chloroperbenzoic acid are added. The mixture is stirred ovemight, theprecipitate is filtered off with suction and the filtrate is admixedwith 0.5 ml of dimethyl sulphide and stirred for 1 hour. 50 ml ofsaturated sodium bicarbonate solution are added and the mixture is thenextracted twice with methylene chloride and the extract is dried andconcentrated. The residue is stirred with isopropanol and the crystalsare filtered off with suction.

Yield: 4.9 g ( 94% of theory), m.p. 187-189° C.

Example XVIII-3′-2 of m.p. 190-193° C. is obtained analogously toExample XVIII-3′-1.

Example XXXVI-1

0.8 g of sodium hydride (60%) is initially charged in 10 ml of anhydrousdimethylformamide (DMF), and, at 0° C., 3.86 g of2,6-dichlorobenzylmercaptan in 10 ml of anhydrous DMF are addeddropwise. After 30 minutes, 2.42 g of 2-fluorobenzonitrile are addeddropwise at 0° C., the mixture is stirred at room temperature overnightand then poured into water and filtered off with suction, and theresidue is stirred with isopropanol, again filtered off with suction anddried.

Yield: 4.89 g ( 83% of theory), m.p. 111° C.

Example XXXVI-2 of m.p. 146° C. is obtained analogously to ExampleXXXVI-1.

Example XXXI-23

1.42 g (10 mmol) of methyl cyclopentanonecarboxylate, 2 g (12 mmol) of2,4,6-trimethylbenzyl mercaptan and 1.9 g (10 mmol) ofp-toluenesulphonic acid hydrate in 20 ml of acetic acid are stirred atroom temperature overnight. The mixture is poured into water and thesolid is filtered off with suction, washed with water and cleaner'snaphtha and dried in the air.

Yield: 0.914 g (31.5% of theory), m.p. 139° C.

The following compounds of the formula (XXXI) were prepared analogouslyto Example XXXI-23 and/or in accordance with the general statements onthe preparation of compounds of formula (XXXI) (variant 2):

TABLE 12 (XXXI)

Ex. No. V W X Y Z A Q¹ R¹² m.p. ° C. XXXI-24 H Cl Cl H H —(CH₂)₃— CH₃152 XXXI-25 Cl Cl H H H —(CH₂)₃— CH₃ oil XXXI-26 H H Cl Cl H —(CH₂)₃—CH₃ 129 XXXI-27 H H OCH₃ CH₃ Cl —(CH₂)₃— CH₃ oil XXXI-29 H CH₃ CH₃ CH₃ H—(CH₂)₄— C₂H₅ oil XXXI-30 H CH₃ CH₃ CH₃ H —(CH₂)₂—C(CH₃)₂—CH₂ CH₃  87

USE EXAMPLES Example A

Nephotettix Test

Solvent: 7 parts by weight of dimethylfornamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Rice seedlings (Oryza sativa) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with the green rice leaf hopper (Nephotettix cincticeps)whilst the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all leaf hoppers have been killed; 0% means that none of theleaf hoppers have been killed.

In this test, for example, the compounds of Preparation Examples I-1-a-1and I-1-a-11 effect, at an exemplary active compound concentration of0.1%, a kill of 100% after 6 days.

Example B

Plutella Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the diamondback moth (Plutellaxylostella) while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the compounds of Preparation Example I-1-i-5exhibits, at an exemplary active compound concentration of 0.1%, a killof 100% after 7 days.

Example C

Plutella test/synthetic Feed

Solvent:  100 parts by weight of acetone Emulsifier: 1900 parts byweight of methanol

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with methanol to the desired concentrations.

A stated amount of the preparation of active compound of the desiredconcentration is pipetted onto a standardized amount of synthetic feed.After the methanol has evaporated, a film box lid covered withapproximately 100 Plutella eggs is placed onto each cavity. The freshlyhatched larvae migrate onto the treated synthetic feed.

In this test, for example, the compound of Preparation Example I-2-i-3exhibited, at an exemplary active compound concentration of 0.1%, aneffect of 95% after 7 days.

What is claimed is:
 1. A compound of the formula (I)

wherein V, W, X, Y and Z independently of one another each representhydrogen, halogen, nitro, cyano or a radical from the group consistingof alkyl, alkenyl, alkinyl, alkoxy, S(O)_(n)-alkyl, halogenoalkyl,halogenoalkoxy, in each case optionally substituted aryl, phenylalkyl,aryloxy, phenyl-alkyloxy or aryl-S(O)_(n)—, where two adjacent radicalstogether with the carbon atoms to which they are attached form anoptionally substituted ring which is optionally interrupted by one ormore heteroatoms and with the proviso that at least one of V, W, X, Y orZ is not hydrogen; n represents the numbers 0 to 2; m represents thenumbers 1 and 2;

A represents hydrogen, in each case optionally halogen-substituted alky,alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated orunsaturated, optionally substituted cycloalkyl in which optionally atleast one ring atom is replaced by a heteroatom, or represents in eachcase optionally halogen-, alkyl-, halogenoalkyl-, alkoxy-,halogenoalkoxy-, cyano- or nitro-substituted aryl, arylalkyl or hetaryl;B represents hydrogen, alkyl or alkoxyalkyl, or A and B together withthe carbon atom to which they are attached represent a saturated orunsaturated, unsubstituted or substituted cycle which optionallycontains at least one heteroatom, D represents hydrogen or an optionallysubstituted radical from the group consisting of alkyl, alkenyl,alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkyl-thioalkyl, saturated orunsaturated, optionally substituted cycloalkyl in which optionally oneor more ring members are replaced by hetero-atoms, or representsoptionally substituted arylalkyl, aryl, hetarylalkyl, hetaryl or CO—R¹¹,or A and D together with the atoms to which they are attached representa saturated or unsaturated cycle which is unsubstituted or substitutedin the A,D-moiety and optionally contains at least one heteroatom, and Grepresents (a) hydroxyl or represents one of the groups

 wherein E represents a metal ion or an ammonium ion, L representsoxygen or sulphur, M represents oxygen or sulphur, R¹ represents in eachcase optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl,alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl- oralkoxy-substituted cycloalkyl in which one or more methylene groups maybe replaced by heteroatoms, or represents in each case optionallysubstituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl orhetaryloxyalkyl, R² represents in each case optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl orrepresents in each case optionally substituted cycloalkyl, phenyl orbenzyl, R³, R⁴ and R⁵ independently of one another each represent ineach case optionally halogen-substituted alkyl, alkoxy, alkylamino,dialkylamino, alkylthio, alkenylthio, cycloalkylthio and represent ineach case optionally substituted phenyl, benzyl, phenoxy or phenylthio,and R⁶ and R⁷ independently of one another each represent hydrogen, ineach case optionally halogen-substituted alkyl, cycloalkyl, alkenyl,alkoxy, alkoxyalkyl, represent optionally substituted phenyl, representoptionally substituted benzyl, or together with the N atom to which theyare attached represent an optionally substituted ring which isoptionally interrupted by oxygen or sulphur, R⁸ represents in each caseoptionally halogen-substituted alkyl, alkoxyalkyl, alkenyl,alkenyloxyalkyl, alkinyl, alkinyloxyalkyl, alkylcarbonylalkyl,alkoxycarbonylalkyl or represents optionally substituted cycloalkyl orrepresents optionally substituted arylalkyl, arylcarbonylalkyl orphenoxyalkyl, and R⁹ and R¹⁰ independently of one another each representhydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, representcycloalkyl which is optionally interrupted by heteroatoms, or representin each case optionally substituted phenyl, phenylalkyl, phenoxyalkyl,hetaryl or hetarylalkyl, or R⁹ and R¹⁰ together with the nitrogen towhich they are attached form a 3- to 9-membered ring which is optionallysubstituted and optionally interrupted by further heteroatoms, or R¹⁰represents the group CO—R¹¹, where R¹¹ represents hydrogen, optionallyhalogen-substituted alkyl, alkenyl, alkoxy, optionally substitutedcycloalkyl which may optionally be interrupted by heteroatoms, orrepresents optionally substituted aryl, arylalkyl, arylalkyloxy orphenoxy, substituents being halogen, nitro, cyano, alkyl, alkoxy,halogenoalkyl and halogenoalkoxy.
 2. The compound of claim 1, wherein Vrepresents hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl,C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy, phenyl, nitro or cyano, W representshydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy,C₁-C₆-halogenoalkoxy, nitro or cyano, X represents hydrogen, halogen,C₁-C₆-alkyl, C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,C₂-C₆-alkinyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl,C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkoxy, nitro, cyano or representsin each case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, phenyl-C₁-C₄-alkyl, phenoxy, phenylthio, benzyloxy orbenzylthio, Y and Z independently of one another each representhydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy,C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl,C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkoxy, nitro, cyano or in each caseoptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₆-halogenoalkoxy-, nitro- or cyano-substituted phenyl,phenyl-C₁-C₄-alkyl, phenoxy, phenylthio, benzyloxy or benzylthio, X andV together with the carbon atoms to which they are attached represent anoptionally halogen- or alkyl-substituted 5- or 6-membered ring which mayoptionally be interrupted by one or two heteroatoms, with the provisothat Y and Z do not form a ring, Y and Z together with the carbon atomsto which they are attached represent an optionally halogen- oralkyl-substituted 5- or 6-membered ring which may optionally beinterrupted by one or two heteroatoms, with the proviso that X and V donot form a ring, m represents the numbers 1 and 2, with the proviso thatat least one of V, W, X, Y or Z is not hydrogen;

 wherein A represents hydrogen or in each case optionallyhalogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₁-C₁₀-alkoxy-C₁-C₈-alkyl, di-, tri- or tetra-C₁-C₈-alkoxy-C₁-C₈-alkyl,C₁-C₁₀-alkylthio-C₁-C₆-alkyl, optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one or twonot directly adjacent ring members are replaced by oxygen and/orsulphur, or represents in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano- ornitro-substituted C₆- or C₁₀-aryl (phenyl or naphthyl), hetaryl having 5to 6 ring atoms or C₆- or C₁₀-aryl-C₁-C₆-alkyl (phenyl-C₁-C₆-alkyl ornaphthyl-C₁-C₆-alkyl), B represents hydrogen, C₁-C₁₂-alkyl orC₁-C₈-alkoxy-C₁-C₆-alkyl, or A, B and the carbon atom to which they areattached represent saturated C₃-C₁₀-cycloalkyl or unsaturatedC₅-C₁₀-cycloalkyl in which optionally one ring member is replaced byoxygen or sulphur and which are optionally mono- or disubstituted byC₁-C₈-alkyl, C₃-C₁₀-cycloalkyl, C₁-C₈-halogenoalkyl, C₁-C₈-alkoxy,C₁-C₈-alkylthio, halogen or phenyl, or A, B and the carbon atom to whichthey are attached represent C₃-C₆-cycloalkyl which is substituted by analkylenediyl group which optionally contains one or two not directlyadjacent oxygen and/or sulphur atoms, or by an alkylenedioxyl or by analkylenedithioyl group which, together with the carbon atom to which itis attached, forms a further five- to eight-membered ring, or A, B andthe carbon atom to which they are attached represent C₃-C₈-cycloalkyl orC₅-C₈-cycloalkenyl in which two substituents together with the carbonatoms to which they are attached represent in each case optionallyC₁-C₆-alkyl-, C₁-C₆-alkoxy- or halogen-substituted C₂-C₆-alkanediyl,C₂-C₆-alkenediyl or C₄-C₆-alkanedienediyl in which optionally onemethylene group is replaced by oxygen or sulphur, D represents hydrogen,in each case optionally halogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₃-C₈-alkinyl, C₁-C₁₀-alkoxy-C₂-C₈-alkyl, di-, tri- ortetra-C₁-C₈-alkoxy-C₂-C₈-alkyl, C₁-C₁₀-alkylthio-C₂-C₈-alkyl, optionallyhalogen-, C₁-C₄-alkyl-, C₁-C₄-alkoxy- or C₁-C₄-halogenoalkyl-substitutedC₃-C₈-cycloalkyl in which optionally one ring member is replaced byoxygen or sulphur, or represents in each case optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkoxy-, cyano- or nitro-substituted phenyl, hetarylhaving 5 or 6 ring atoms, phenyl-C₁-C₆-alkyl or hetaryl-C₁-C₆-alkylhaving 5 or 6 ring atoms or represents the group CO—R¹¹, or A and Dtogether represent in each case optionally substituted C₃-C₆-alkanediylor C₃-C₆-alkenediyl in which optionally one methylene group is replacedby a carbonyl group, oxygen or sulphur, substituents being in each casehalogen, hydroxyl, mercapto or in each case optionallyhalogen-substituted C₁-C₁₀-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₃-C₇-cycloalkyl, phenyl or benzyloxy, where optionally two adjacentsubstituents together with the carbon atoms to which they are attachedform a further saturated or unsaturated cycle having 5 or 6 ring atoms(in the case of the compound of the formula (I-1), A and D thenrepresent, together with the atoms to which they are attached, thegroups AD-1 to AD-10 mentioned further below) which may contain oxygenor sulphur, or which may optionally contain one of the following groups

G represents hydroxyl (a) or represents one of the groups

 in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur and M represents oxygen or sulphur, R¹ represents ineach case optionally halogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkyl-thio-C₁-C₈-alkyl,poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one ormore not directly adjacent ring members are replaced by oxygen and/orsulphur, represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-, C₁-C₆-halogenoalkoxy-,C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl, representsoptionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl, represents optionally halogen- orC₁-C₆-alkyl-substituted 5- or 6-membered hetaryl, represents optionallyhalogen- or C₁-C₆-alkyl-substituted phenoxy-C₁-C₆-alkyl, or representsoptionally halogen-, amino- or C₁-C₆-alkyl-substituted 5- or 6-memberedhetaryloxy-C₁-C₆-alkyl, R² represents in each case optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl, representsoptionally halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substitutedC₃-C₈-cycloalkyl, or represents in each case optionally halogen-,cyano-, nitro-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- orC₁-C₆-halogenoalkoxy-substituted phenyl or benzyl, R³ representsoptionally halogen-substituted C₁-C₈-alkyl or represents in each caseoptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl, R⁴and R⁵ independently of one another each represent in each caseoptionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio,C₂-C₈-alkenylthio, C₃-C₇-cycloalkylthio or represent in each caseoptionally halogen-, nitro-, cyano-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkyl- or C₁-C₄-halogenoalkyl-substituted phenyl, phenoxy orphenylthio, R⁶ and R⁷ independently of one another each representhydrogen, represent in each case optionally halogen-substitutedC₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, represent optionally halogen-,C₁-C₈-halogenoalkyl-, C₁-C₈-alkyl- or C₁-C₈-alkoxy-substituted phenyl,optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- orC₁-C₈-alkoxy-substituted benzyl or together with the N atom to whichthey are attached represent an optionally C₁-C₄-alkyl-substitutedC₃-C₆-alkylene radical in which optionally one carbon atom is replacedby oxygen or sulphur, R⁸ represents in each case optionallyhalogen-substituted C₁-C₁₀-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkinyl,C₁-C₈-alkoxy-C₁-C₄-alkyl, C₃-C₈-alkenyloxy-C₁-C₄-alkyl,C₃-C₈-alkinyloxy-C₁-C₄-alkyl, C₁-C₈-alkylcarbonyl-C₁-C₄-alkyl,C₁-C₈-alkoxycarbonyl-C₁-C₄-alkyl, represents optionally fluorine-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted cycloalkyl or representsoptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl-C₁-C₄-alkyl,phenylcarbonyl-C₁-C₄-alkyl or phenoxy-C₁-C₄-alkyl, R⁹ representshydrogen, optionally halogen-substituted C₁-C₁₀-alkyl, C₃-C₁₀-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl, cycloalkyl having3 to 8 ring atoms which may be interrupted by an oxygen or sulphur atom,represents phenyl, phenyl-C₁-C₆-alkyl or phenoxy-C₁-C₆-alkyl orhetaryl-C₁-C₆-alkyl having in each case 5 or 6 ring atoms, where thering contains 1 or 2 identical or different oxygen, nitrogen and sulphuratoms, each of which is optionally mono- to trisubstituted by identicalor different substituents from the group consisting of halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,cyano and nitro, or R¹⁰ represents hydrogen, C₁-C₁₀-alkyl,C₃-C₁₀-alkenyl or represents a group CO—R¹¹, or R⁹ and R¹⁰ together withthe nitrogen atom to which they are attached represent an optionallyC₁-C₄-alkyl-substituted three- to seven-membered saturated ring in whichoptionally one methylene group which is not directly adjacent to thenitrogen atom may be replaced by an oxygen or sulphur atom, R¹¹represents hydrogen, in each case optionally halogen-substitutedC₁-C₁₀-alkyl, C₃-C₁₀-alkenyl, C₁-C₁₀-alkoxy, optionally halogen-,C₁-C₄-alkyl-, C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl or representsoptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkoxy-, cyano- or nitro-substituted phenyl,phenyl-C₁-C₆-alkyl, benzyloxy or phenoxy, R¹⁶ represents hydrogen,represents in each case optionally halogen-substituted C₁-C₈-alkyl orC₁-C₈-alkoxy, represents optionally halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur, or represents in eachcase optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkoxy, R¹⁷ representshydrogen or C₁-C₈-alkyl, or R¹⁶ and R¹⁷ represent C₄-C₆-alkanediyl, R¹⁸and R¹⁹ are identical or different and each represents C₁-C₆-alkyl, orR¹⁸ and R¹⁹ together represent a C₂-C₄-alkanediyl radical which isoptionally substituted by C₁-C₆-alkyl, C₁-C₆-halogenoalkyl or byoptionally halogen-, C₁-C₆-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, R²⁰ and R²¹independently of one another each represent hydrogen, representoptionally halogen-substituted C₁-C₈-alkyl or represent optionallyhalogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, or R²⁰ andR²¹ together with the carbon atom to which they are attached represent acarbonyl group or represent optionally halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₅-C₇-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur, and R²² and R²³independently of one another each represent C₁-C₁₀-alkyl,C₂-C₁₀-alkenyl, C₁-C₁₀-alkoxy, C₁-C₁₀-alkylamino, C₃-C₁₀-alkenylamino,di-(C₁-C₁₀-alkyl)amino or di-(C₃-C₁₀-alkenyl)amino.
 3. The compound ofclaim 1, wherein X represents hydrogen, fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,nitro or cyano or represents in each case optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy orbenzyloxy, V represents hydrogen, fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy,phenyl, nitro or cyano, W represents hydrogen, fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy,C₁-C₄-halogenoalkoxy, nitro or cyano, Y and Z independently of oneanother each represent hydrogen, fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy,cyano, nitro or represent in each case optionally fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₂-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₂-halogenoalkoxy-, cyano- or nitro-substituted phenyl, phenoxy orbenzyloxy, X and V together with the carbon atoms to which they areattached represent an optionally fluorine-, chlorine- orC₁-C₄-alkyl-substituted 5- or 6-membered ring which may optionally beinterrupted by two not directly adjacent oxygen atoms, with the provisothat Y and Z do not form a ring, Y and Z together with the carbon atomsto which they are attached represent an optionally fluorine-, chlorine-or C₁-C₄-alkyl-substituted 5- or 6-membered ring which may optionally beinterrupted by one or two oxygen atoms, with the proviso that X and V donot form a ring, and with the proviso that at least one of V, W, X, Y orZ is not hydrogen; m represents the numbers 1 and 2;

 wherein A represents hydrogen, in each case optionally fluorine- orchlorine-substituted C₁-C₁₀-alkyl, C₁-C₈-alkoxy-C₁-C₆-alkyl, optionallyfluorine-, chlorine-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substitutedC₃-C₇-cycloalkyl in which optionally one ring member is replaced byoxygen or sulphur, or represents phenyl or phenyl-C₁-C₂-alkyl, each ofwhich is optionally mono- to disubstituted by fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₂-halogenoalkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkoxy, cyano or nitro, B represents hydrogen orC₁-C₆-alkyl, or A, B and the carbon atom to which they are attachedrepresent saturated or unsaturated C₅-C₇-cycloalkyl in which optionallyone ring member is replaced by oxygen or sulphur and which is optionallymonosubstituted by C₁-C₆-alkyl, C₅-C₆-cycloalkyl, C₁-C₂-halogenoalkyl,C₁-C₆-alkoxy, fluorine, chlorine or phenyl, or A, B and the carbon atomto which they are attached represent C₅-C₆-cycloalkyl which issubstituted by an alkylenediyl group which optionally contains one ortwo not directly adjacent oxygen or sulphur atoms or by analkylenedioxyl or by an alkylenedithiol group which, together with thecarbon atom to which it is attached, forms a further 5- or 6-memberedring, or A, B and the carbon atom to which they are attached representC₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in which two substituentstogether with the carbon atoms to which they are attached representC₂-C₄-alkanediyl, C₂-C₄-alkenediyl, in which optionally one methylenegroup is replaced by oxygen or sulphur, or butadienediyl, each of whichis optionally substituted by C₁-C₅-alkyl, C₁-C₅-alkoxy, fluorine,chlorine or bromine, D represents hydrogen, represents in each caseoptionally fluorine- or chlorine-substituted C₁-C₈-alkyl, C₃-C₆-alkenyl,C₁-C₆-alkoxy-C₂-C₄-alkyl or C₁-C₆-alkylthio-C₂-C₄-alkyl, representsoptionally fluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy- orC₁-C₂-halogenoalkyl-substituted C₃-C₇-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur, or represents phenylor phenyl-C₁-C₂-alkyl, each of which is optionally mono- todisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₂-halogenoalkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkoxy, cyano or nitro,or represents the group CO—R¹¹, or A and D together represent optionallysubstituted C₃-C₅-alkanediyl in which one methylene group may bereplaced by a carbonyl group, oxygen or sulphur, substituents beinghydroxyl, C₁-C₆-alkyl or C₁-C₄-alkoxy, or A and D (in the case of thecompounds of formula (I-1)) together with the atoms to which they areattached represent one of the groups AD-1 to AD-10:

G represents hydroxyl (a) or represents one of the groups

 in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur and M represents oxygen or sulphur, R¹ representsC₁-C₁₆-alkyl, C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkylthio-C₁-C₄-alkyl, each of which is optionally mono- totrisubstituted by fluorine or chlorine, or represents optionallyfluorine-, chlorine-, C₁-C₅-alkyl- or C₁-C₅-alkoxy-substitutedC₃-C₆-cycloalkyl in which optionally one or two not directly adjacentring members are replaced by oxygen and/or sulphur, represents phenylwhich is optionally mono- to disubstituted by fluorine, chlorine,bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, C₁-C₂-alkylthio or C₁-C₂-alkylsulphonyl,represents phenyl-C₁-C₄-alkyl which is optionally mono- to disubstitutedby fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₃-halogenoalkyl or C₁-C₃-halogenoalkoxy, or represents pyrazolyl,thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which isoptionally mono- to disubstituted by fluorine, chlorine, bromine orC₁-C₄-alkyl, R² represents C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl orC₁-C₆-alkoxy-C₂-C₆-alkyl, each of which is optionally mono- totrisubstituted by fluorine, or represents phenyl or benzyl, each ofwhich is optionally mono- to disubstituted by fluorine, chlorine,bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₃-alkoxy, C₁-C₂-halogenoalkyl orC₁-C₂-halogenoalkoxy, R³ represents C₁-C₆-alkyl which is optionallymono- to trisubstituted by fluorine, or represents phenyl which isoptionally mono- to disubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,cyano or nitro, R⁴ and R⁵ independently of one another each representC₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino,C₁-C₆-alkylthio, C₃-C₄-alkenylthio, C₃-C₆-cycloalkylthio or representphenyl, phenoxy or phenylthio, each of which is optionally mono- todisubstituted by fluorine, chlorine, bromine, nitro, cyano,C₁-C₃-alkoxy, C₁-C₃-halogenoalkoxy, C₁-C₃-alkyl or C₁-C₃-halogenoalkyl,R⁶ represents C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, represents phenyl which isoptionally mono- to disubstituted by fluorine, chlorine, bromine,C₁-C₃-halogenoalkyl, C₁-C₄-alkyl or C₁-C₄-alkoxy, represents benzylwhich is optionally mono- to disubstituted by fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₃-halogenoalkyl or C₁-C₄-alkoxy, R⁷ representshydrogen, C₁-C₆-alkyl or C₃-C₆-alkenyl, or R⁶ and R⁷ together with thenitrogen atom to which they are attached represent a 5- or 6-memberedring in which optionally one methylene group not directly adjacent tothe nitrogen atom may be replaced by an oxygen or sulphur atom and whichis optionally mono- to disubstituted by methyl or ethyl, R⁸ representsC₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkinyl, C₁-C₆-alkoxy-C₁-C₂-alkyl,C₃-C₆-alkenyloxy-C₁-C₂-alkyl, C₃-C₈-alkinyloxy-C₁-C₂-alkyl,C₁-C₆-alkylcarbonyl-C₁-C₂-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₂-alkyl, eachof which is optionally mono- to trisubstituted by fluorine or chlorine,or represents phenyl-C₁-C₂-alkyl, phenylcarbonyl-C₁-C₄-alkyl orphenoxy-C₁-C₂-alkyl, each of which is optionally mono- to disubstitutedby fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, cyano or nitro, R⁹ representshydrogen, represents C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-cycloalkyl,each of which is optionally mono- to trisubstituted by fluorine orchlorine, represents phenyl-C₁-C₂-alkyl or pyridyl-C₁-C₂-alkyl, each ofwhich is optionally mono- to disubstituted by fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, cyano or nitro, R¹⁰ represents hydrogen,C₁-C₆-alkyl, C₃-C₆-alkenyl or represents a group CO—R¹¹, or R⁹ and R¹⁰together with the nitrogen atom to which they are attached represent asaturated 5- or 6-membered ring in which optionally a methylene groupwhich is not directly adjacent to the nitrogen atom may be replaced byan oxygen or sulphur atom and which is optionally mono- to disubstitutedby methyl or ethyl, and R¹¹ represents hydrogen, represents C₁-C₆-alkyl,C₃-C₆-alkenyl, C₁-C₆-alkoxy, each of which is optionally mono- totrisubstituted by fluorine or chlorine, represents C₃-C₆-cycloalkylwhich is optionally mono- to disubstituted by fluorine, chorine, methyl,ethyl, methoxy or ethoxy or represents phenyl which is optionally mono-to disubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, cyano or nitro.4. The compound of claim 1, wherein V represents hydrogen, fluorine,chlorine, bromine, nitro, methyl, phenyl, methoxy or trifluoromethyl, Wrepresents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,trifluoromethyl, methoxy, X represents hydrogen, bromine, fluorine,chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy,n-propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy,trifluoromethoxy, nitro or cyano, or represents phenyl, phenoxy orbenzyloxy, each of which is optionally mono- to disubstituted byfluorine, chlorine, bromine, methyl, tert-butyl, trifluoromethyl,methoxy, trifluoromethoxy, nitro or cyano, Y represents hydrogen,fluorine, chlorine, bromine, methyl, ethyl, i-propyl, tert-butyl,trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy,trifluoromethoxy, difluoromethoxy, cyano, nitro or represents phenylwhich is optionally mono- to disubstituted by fluorine, chlorine,bromine, methyl, trifluoromethyl, methoxy, trifluoromethoxy, cyano ornitro, Z represents hydrogen, fluorine, chlorine, bromine, methyl,trifluoromethyl, methoxy, trifluoromethoxy, cyano, nitro or representsphenyl which is optionally mono- to disubstituted by fluorine, chlorine,bromine, methyl, trifluoromethyl, methoxy, trifluoromethoxy, cyano ornitro, X and V together with the carbon atoms to which they are attachedrepresent an optionally fluorine- or methyl-substituted 5- or 6-memberedring which is interrupted by two not directly adjacent oxygen atoms,with the proviso that Y and Z do not form a ring, Y and Z together withthe carbon atoms to which they are attached represent an optionallyfluorine- or methyl-substituted 5- or 6-membered ring which may beinterrupted by one or two not directly adjacent oxygen atoms, with theproviso that X and V do not form a ring, m represents the number 2, withthe proviso that at least one of V, W, X, Y or Z is not hydrogen;

 wherein A represents hydrogen, optionally fluorine-substitutedC₁-C₆-alkyl, optionally fluorine-, methyl- or methoxy-substitutedC₃-C₆-cycloalkyl or represents phenyl or benzyl, each of which isoptionally mono- to disubstituted by fluorine, chlorine, bromine,methyl, iso-propyl, tert-butyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro, B represents hydrogen or C₁-C₄-alkyl,or A, B and the carbon atom to which they are attached representsaturated C₅-C₆-cycloalkyl in which optionally one ring member isreplaced by oxygen or sulphur and which is optionally monosubstituted bymethyl, ethyl, n-propyl, isopropyl, butyl, iso-butyl, sec-butyl,tert-butyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, iso-propoxy,n-butoxy, iso-butoxy, fluorine or chlorine, or A, B and the carbon atomto which they are attached represent C₅-C₆-cycloalkyl in which twosubstituents together with the carbon atoms to which they are attachedrepresent C₂-C₄-alkanediyl or C₂-C₄-alkenediyl in which in each caseoptionally one methylene group is replaced by oxygen or sulphur, orrepresent butadienediyl, D represents hydrogen, represents in each caseoptionally fluorine- or chlorine-substituted C₁-C₆-alkyl, C₃-C₄-alkenyl,C₁-C₄-alkoxy-C₂-C₃-alkyl, C₁-C₄-alkylthio-C₂-alkyl or C₃-C₆-cycloalkylin which optionally one methylene group is replaced by oxygen orsulphur, or represents phenyl or benzyl, each of which is optionallymono- to disubstituted by fluorine, chlorine, bromine, methyl, ethyl,n-propyl, iso-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro, or represents the group CO—R¹¹, or Aand D together represent optionally substituted C₃-C₄-alkanediyl inwhich optionally one carbon atom is replaced by sulphur and which isoptionally substituted by methyl, or A and D (in the case of thecompounds of the formula (I-1)) together with the atoms to which theyare attached represent one of the groups AD-1 to

G represents hydroxyl (a) or represents one of the groups

 in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur and M represents oxygen or sulphur, R¹ representsC₁-C₁₄-alkyl, C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkylthio-C₁-C₂-alkyl, each of which is optionally mono- totrisubstituted by fluorine or chlorine, or represents C₃-C₆-cycloalkylin which optionally one or two not directly adjacent ring members arereplaced by oxygen and which is optionally mono- to disubstituted byfluorine, chlorine, methyl, ethyl, i-propyl, i-butyl, tert-butyl,methoxy, ethoxy or iso-propoxy, represents phenyl which is optionallymono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro,methyl, ethyl, i-propyl, methoxy, ethoxy, trifluoromethyl ortrifluoromethoxy, or represents furanyl, thienyl or pyridyl, each ofwhich is optionally mono- to disubstituted by fluorine, chlorine,bromine, methyl or ethyl, R² represents C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl orC₁-C₄-alkoxy-C₂-C₄-alkyl, each of which is optionally mono- totrisubstituted by fluorine, or represents phenyl or benzyl, each ofwhich is optionally mono- to disubstituted by fluorine, chlorine, cyano,nitro, methyl, ethyl, i-propyl, methoxy, ethoxy, trifluoromethyl ortrifluoromethoxy, R³ represents methyl, ethyl, n-propyl, isopropyl, eachof which is optionally mono- to trisubstituted by fluorine, orrepresents phenyl which is optionally monosubstituted by fluorine,chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro, R⁴ and R⁵ independently of one anothereach represent C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,di-(C₁-C₄-alkyl)amino, C₁-C₄-alkylthio or represent phenyl, phenoxy orphenylthio, each of which is optionally mono- to disubstituted byfluorine, chlorine, bromine, methyl, nitro, cyano, methoxy,trifluoromethoxy or trifluoromethyl, R⁶ represents C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,represents phenyl which is optionally mono- to disubstituted byfluorine, chlorine, bromine, trifluoromethyl, methyl or methoxy,represents benzyl which is optionally mono- to disubstituted byfluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy, R⁷represents hydrogen, C₁-C₄-alkyl or C₃-C₄-alkenyl, or R⁶ and R⁷ togetherwith the nitrogen atom to which they are attached represent a 5- or6-membered ring in which optionally one methylene group which is notdirectly adjacent to the nitrogen atom may be replaced by an oxygen orsulphur atom and which is optionally mono- to disubstituted by methyl,R⁸ represents C₁-C₄-alkyl, C₃-C₄-alkenyl, C₁-C₄-alkoxy-methyl,C₃-C₄-alkenyloxy-methyl, C₃-C₄-alkinyloxy-methyl,C₁-C₄-alkylcarbonyl-methyl, C₁-C₄-alkoxycarbonyl-methyl, each of whichis optionally mono- to trisubstituted by fluorine or chlorine, orrepresents benzyl, phenylcarbonyl-methyl or phenoxy-methyl, each ofwhich is optionally mono- to disubstituted by fluorine, chlorine,bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano ornitro, R⁹ represents hydrogen, represents C₁-C₄-alkyl, ally,cyclopropyl, cyclopentyl, cyclohexyl, each of which is optionally mono-to trisubstituted by fluorine or chlorine, represents benzyl which isoptionally mono- to disubstituted by fluorine, chlorine, bromine,methyl, ethyl, iso-propyl, tert-butyl, methoxy, iso-propoxy,trifluoromethyl, trifluoromethoxy, cyano or nitro, R¹⁰ representshydrogen, C₁-C₄-alkyl, allyl or represents a group CO—R¹¹, or R⁹ and R¹⁰together with the nitrogen atom to which they are attached represent asaturated 5- to 6-membered ring in which optionally one methylene groupwhich is not directly adjacent to the nitrogen atom may be replaced byan oxygen or sulphur atom and which is optionally mono- to disubstitutedby methyl, and R¹¹ represents hydrogen, represents C₁-C₄-alkyl,C₃-C₄-alkenyl, C₁-C₄-alkoxy, each of which is optionally mono- totrisubstituted by fluorine or chlorine, represents cyclopropyl,cyclopentyl or cyclohexyl, each of which is optionally monosubstitutedby fluorine, chlorine, methyl or methoxy, or represents phenyl which isoptionally mono- to disubstituted by fluorine, chlorine, bromine,methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro. 5.The compound of claim 1, wherein V represents hydrogen, fluorine,chlorine, bromine, methyl, trifluoromethyl, nitro or phenyl, Wrepresents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, Xrepresents hydrogen, fluorine, chlorine, bromine, methyl, methoxy,ethyl, n-propyl, iso-propyl, ethoxy, n-propoxy, iso-propoxy,trifluoromethyl, nitro or cyano, Y represents hydrogen, fluorine,chlorine, bromine, methyl, ethyl, iso-propyl, tert-butyl, methoxy,ethoxy, iso-propoxy, difluoromethyl, trifluoromethyl, trifluoromethoxy,difluoromethoxy or phenyl, Z represents hydrogen, fluorine, chlorine,bromine, methyl, trifluoromethyl, Y and Z together with the carbon atomsto which they are attached form a 5-membered ring which may beinterrupted by one or two not directly adjacent oxygen atoms, with theproviso that X and V do not form a ring, m represents 2, with theproviso that at least of the substituents V, W, X, Y or Z is nothydrogen,

 in which A represents hydrogen, C₁-C₄-alkyl, represents phenyl orbenzyl, each of which is optionally mono- to disubstituted by chlorineor fluorine, B represents hydrogen or C₁-C₄-alkyl, A and B and thecarbon atom to which they are attached represent saturated cyclohexyl inwhich optionally one ring member is replaced by oxygen and which isoptionally substituted by methyl, ethyl, n-propyl, isopropyl, butyl,iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, methoxy, ethoxy,n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, fluorine or chlorine, Drepresents hydrogen, C₁-C₄-alkyl, represents phenyl or benzyl, each ofwhich is optionally mono- or disubstituted by chlorine, fluorine,bromine, or represents a group CO—R¹¹, and G represents hydroxyl (a) orrepresents

 wherein R¹ represents C₁-C₈-alkyl, R² represents C₁-C₈-alkyl, L and Meach represent oxygen, R⁹ represents hydrogen, R¹⁰ represents hydrogenor represents a group CO—R¹¹, R¹¹ represents C₁-C₄-alkyl.
 6. A processfor preparing the compound of claim 1, characterized in that, to obtain(A) compounds of the formula (I-1-a)

wherein A, B, D, V, W, X, Y, Z and m are each as defined in claim 1,pounds of the formula (II)

 in which A, B, D, V, W, X, Y, Z and m are each as defined in claim 1and R¹² represents alkyl are condensed intramolecularly in the presenceof a diluent and in the presence of a base; and the resulting compoundsof the formula I-1-a are, if appropriate, subsequently (1) (α) reactedwith compounds of the formula (VI)

 in which R¹ is as defined above and Hal represents halogen or (β)reacted with compounds of the formula (VII) R¹—CO—O—CO—R¹  (VII) inwhich R¹ is as defined above, if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder; (2)reacted with compounds of the formula (VIII) R²—M—CO—Cl  (VIII) in whichR² and M are each as defined above, if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder; (3)reacted with compounds of the formula (IX)

in which M and R² are each as defined above, if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder, (4) reacted with compounds of the formula (X) R³—SO₂—Cl  (X) inwhich R³ is as defined above, if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder, (5)reacted with compounds of the formula (XI)

 in which L, R⁴ and R⁵are each as defined above and Hal representshalogen, if appropriate in the presence of a diluent and if appropriatein the presence of an acid binder, (6) reacted with compounds of theformula (XII) or (XIII) Me(OR¹³)_(t)  (XII)

 in which Me represents a mono- or divalent metal, t represents thenumber 1 or 2 and R¹³, R¹⁴, R¹⁵ independently of one another eachrepresent hydrogen or alkyl, if appropriate in the presence of adiluent, (7) (α) reacted with compounds of the formula (XIV)R⁶—N═C═L  (XIV) in which R⁶ and L are each as defined above, ifappropriate in the presence of a diluent and if appropriate in thepresence of a catalyst, or (β) reacted with compounds of the formula(XV)

in which L, R⁶ and R⁷ are each as defined above, if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder, (8) reacted with compounds of the formula (XVI) R¹⁰—U  (XVI), in which R¹⁰ is as defined above, U represents chlorine, bromine,iodine and O—SO₂—R¹⁶ and R¹⁶ represents optionally halogen-substitutedalkyl or optionally substituted phenyl, if appropriate in the presenceof a diluent and if appropriate in the presence of an acid binder, (9)(α) reacted with compounds of the formula (XVII)

in which R⁹ and R¹⁰ are each as defined above and R¹⁰ does not representthe group CO—R¹¹, in the presence of a diluent, if appropriate in thepresence of an acidic catalyst, with distillative removal of anazeotrope or in the presence of a dehydrating agent, or (β) in the casethat R⁹ and R¹⁰ each represent hydrogen, compounds of the formula(XVIII)

 in which V, W, X, Y, Z and m are each as defined above and

in which the radicals A, B, and D are each as defined above are cyclizedintramolecularly in the presence of a solvent and in the presence of abase, and the compounds of the formula (I-1-i¹)

in which F¹, F², R⁹, V, W, X, Y, Z and m are each as defined above are,if appropriate, subsequently (10) (α) reacted with compounds of theformula (XIX)

 in which R¹¹ is as defined above, but does not represent hydrogen, Halrepresents halogen, if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder, or (β) reacted withcompounds of the formula (XX) R¹¹-CO—O—CO—R¹¹  (XX) in which R¹¹ are asdefined above and, independently of one another, are identical ordifferent, but do not represent hydrogen, if appropriate in the presenceof a diluent and if appropriate in the presence of an acid binder, italso being possible to use mixtures of the reagents of the formulae(XVIII) and (XIX), or (γ) reacted with compounds of the formula (XXI)

 in which R¹¹ represents hydrogen and Alk represents C₁-C₄-alkyl, ifappropriate in the presence of a diluent and if appropriate in thepresence of a base, and that, to obtain (B) compounds of the formula(I-1-i)

in which A, B, R⁹, R¹⁰, R¹¹, V, W, X, Y, Z and m are each as definedabove, compounds of the formula (I-1-i²)

in which A, B, R⁹, R¹⁰, V, W, X, Y, Z and m are each as defined aboveare reacted with compounds of the formula (XIX)

 in which R¹¹ is as defined above, but does not represent hydrogen, Halrepresents halogen, if appropriate in the presence of a diluent and inthe presence of a base.
 7. A crop protection agent selected from thegroup consisting of pesticides, herbicides and fungicides, comprisingone or more compounds of formula (I) of claim 1 and a member selectedfrom the group consisting of extenders, surfactants and mixturesthereof.
 8. Method for controlling insects, arachnids, nematodes, fungiand undesirable vegetation, comprising allowing one or more compounds ofthe formula (I) of claim 1 to act on said insects, arachnids, nematodes,fungi and undesirable vegetation and/or their habitats.
 9. A process fora preparing a crop protection agent selected from the group consistingof pesticides, herbicides and fungicides, comprising mixing one or morecompounds of the formula (I) of claim 1 with extenders and/orsurfactants.